918340-51-9|4-Chlorofuro[2,3-d]pyrimidine| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 918340-51-9 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 918340-51-9 ]

CAS No. :	918340-51-9
Formula :	C₆H₃ClN₂O
M.W :	154.55
SMILES Code :	ClC1=NC=NC2=C1C=CO2
MDL No. :	MFCD09834941
InChI Key :	RXNNSCCBHMRHIX-UHFFFAOYSA-N
Pubchem ID :	44558543

Safety of [ 918340-51-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 918340-51-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 918340-51-9 ]
Downstream synthetic route of [ 918340-51-9 ]

[ 918340-51-9 ] Synthesis Path-Upstream 1~2

1
[ 186454-70-6 ]
[ 918340-51-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: With chloro-trimethyl-silane; tert.-butylnitrite In acetonitrile at 50℃; for 1.5 h; Stage #2: With sodium hydroxide In water; acetonitrile	4-Chlorofuro[2,3,cflpyrimidine was obtained via modified Sandmeyer reaction²⁵ with 4-amino-furopyrimidine 25.²⁶(²⁵) (a) For the modified Sandmeyer reaction, see: (a) Bracher, F.; Daab, J. Eur. J. Org. Chem. 2002, 2288. (b)Doyle, M. P.; Siegfiied, B.; Dellaria, J. F. J. Org. Chem. 1977, 42, 2426.(²⁶) Nakano, M.; Maeda, Y. WO 2005061516 Al 20050707 CAN 143:115566. EPO <DP n="82"/>The mixture of 4-amino-furopyrimidme 25 (303 mg, 2.24 mmol), tert-butyl nitrite (5.3 niL, 44.6 mmol), TMSCl (1.4 mL, 11.07 mmol) in acetonitrile (5.0 mL) was stirred at 50 ⁰C for 1.5 h. After this period, the mixture was quenched with IN NaOH and the aqueous phase was thoroughly extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na₂SO₄, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with 10percent EtOAc/hexanes to give 26 (139 mg, 40percent).¹H NMR (500 MHz, CDCl₃, δ): 8.68 (s, IH), 7.72 (d, J= 2.5 Hz₅ IH), 6.84 (d, J = 2.5 Hz₅ IH). ¹³C NMR (125 MHz₅ CDCl₃, δ): 167.1, 154.0, 153.5, 146.0, 177.9, 104.7. MS m/z (relative intensity) 154 (M⁺, 100), 119 (37), 98 (21).
22%	With chloro-trimethyl-silane; tert.-butylnitrite In acetonitrile at 50℃; for 1 h;	Step 3. Synthesis of 4-chlorofuro[2,3-d]pyrimidine (C3). A mixture of C2 (660 mg, 4.88 mmol), terf-butyl nitrite (12.1 mL, 97.7 mmol), and trimethylsilyl chloride (3.12 mL, 24.4 mmol) in acetonitrile (20 mL) was stirred at 50 °C for 1 hour. The reaction was cooled to room temperature and quenched with aqueous sodium hydroxide solution (2 M, 30 mL). The aqueous layer was extracted with ethyl acetate (3 x 50 mL), and the combined organic layers were dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified via chromatography on silica gel (Gradient: 0percent to 30percent ethyl acetate in heptane) to provide the product as a volatile white solid. Yield: 168 mg, 1.09 mmol, 22percent. LCMS m/z 154.8 [M+H]⁺. ¹ H NMR (400 MHz, CDCI₃) δ 8.77 (s, 1 H), 7.76 (d, J=0.8 Hz, 1 H), 7.25 (d, J=0.8 Hz, 1 H).

References: [1] Journal of the American Chemical Society, 2006, vol. 128, # 48, p. 15372 - 15373.
[2] Patent: WO2007/38387, 2007, A2, . Location in patent: Page/Page column 80-81.
[3] Patent: WO2015/162518, 2015, A1, . Location in patent: Page/Page column 108.

2
[ 139370-56-2 ]
[ 918340-51-9 ]

References: [1] Patent: WO2015/162518, 2015, A1, .

[ 918340-51-9 ] Synthesis Path-Downstream 1~24

1
[ 186454-70-6 ]
[ 918340-51-9 ]

Yield	Reaction Conditions	Operation in experiment
40%		4-Chlorofuro[2,3,cflpyrimidine was obtained via modified Sandmeyer reaction25 with 4-amino-furopyrimidine 25.26(25) (a) For the modified Sandmeyer reaction, see: (a) Bracher, F.; Daab, J. Eur. J. Org. Chem. 2002, 2288. (b)Doyle, M. P.; Siegfiied, B.; Dellaria, J. F. J. Org. Chem. 1977, 42, 2426.(26) Nakano, M.; Maeda, Y. WO 2005061516 Al 20050707 CAN 143:115566. EPO <DP n="82"/>The mixture of 4-amino-furopyrimidme 25 (303 mg, 2.24 mmol), tert-butyl nitrite (5.3 niL, 44.6 mmol), TMSCl (1.4 mL, 11.07 mmol) in acetonitrile (5.0 mL) was stirred at 50 0C for 1.5 h. After this period, the mixture was quenched with IN NaOH and the aqueous phase was thoroughly extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with 10% EtOAc/hexanes to give 26 (139 mg, 40%).1H NMR (500 MHz, CDCl3, delta): 8.68 (s, IH), 7.72 (d, J= 2.5 Hz5 IH), 6.84 (d, J = 2.5 Hz5 IH). 13C NMR (125 MHz5 CDCl3, delta): 167.1, 154.0, 153.5, 146.0, 177.9, 104.7. MS m/z (relative intensity) 154 (M+, 100), 119 (37), 98 (21).
22%	With chloro-trimethyl-silane; tert.-butylnitrite; In acetonitrile; at 50℃; for 1h;	Step 3. Synthesis of 4-chlorofuro[2,3-d]pyrimidine (C3). A mixture of C2 (660 mg, 4.88 mmol), terf-butyl nitrite (12.1 mL, 97.7 mmol), and trimethylsilyl chloride (3.12 mL, 24.4 mmol) in acetonitrile (20 mL) was stirred at 50 C for 1 hour. The reaction was cooled to room temperature and quenched with aqueous sodium hydroxide solution (2 M, 30 mL). The aqueous layer was extracted with ethyl acetate (3 x 50 mL), and the combined organic layers were dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified via chromatography on silica gel (Gradient: 0% to 30% ethyl acetate in heptane) to provide the product as a volatile white solid. Yield: 168 mg, 1.09 mmol, 22%. LCMS m/z 154.8 [M+H]+. 1 H NMR (400 MHz, CDCI3) delta 8.77 (s, 1 H), 7.76 (d, J=0.8 Hz, 1 H), 7.25 (d, J=0.8 Hz, 1 H).

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 15372 - 15373.
[2]Patent: WO2007/38387,2007,A2 .Location in patent: Page/Page column 80-81.
[3]Patent: WO2015/162518,2015,A1 .Location in patent: Page/Page column 108.

2
[ 918340-51-9 ]
[ 6358-06-1 ]
[ 918340-57-5 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 15372 - 15373.

3
[ 918340-51-9 ]
[4-chloro-3-(3-methyl-but-2-enyloxy)-phenyl]-furo[2,3-<i>d</i>]pyrimidin-4-yl-amine [ No CAS ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 15372 - 15373.

4
[ 918340-51-9 ]
[ 64-18-6 ]
(1r,4r)-1-N,1-N-dimethylcyclohexane-1,4-diamine dihydrochloride [ No CAS ]
N¹-(furo[2,3-d]pyrimidin-4-yl)trans-N⁴,N⁴-dimethylcyclohexane-1,4-diamine*1.18(formic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%		Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of <strong>[918340-51-9]4-chlorofuro[2,3-d]pyrimidine</strong> (60 mg, 0.39 mmol, 1.00 equiv), trans-N,N-dimethylcyclohexane-l ,4-diamine dihydrochloride (314 mg, 1.46 mmol, 3.76 equiv) and triethylamine (0.43 ml, 8.00 equiv) in 10 mL of distilled DMF. The resulting solution was stirred overnight at 50C in an oil bath. After completion, the reaction solution was cooled with an ice-water bath and diluted with ethyl acetate, washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (80 mg) was purified by Prep-HPLC with the following conditions (SHIMADZU): Column, SunFire Prep CI 8, 19* 150mm 5um; mobile phase, water with 1% HCOOH and CH3CN (3.0% CH3CN up to 8% in 10 min); Flow rate: 20 mL/min; UV detection at 254/220 nm. The product-containing fractions were collected and evaporated to remove solvents under reduced pressure to give 38.9 mg (33%) of the resulted N1-(furo[2,3-d]pyrimidin-4-yl)-tra/?5-N4,N4- dimethylcyclohexane-l ,4-diamine formate as an off-white solid. LCMS (ES, m/z): 261 [M- 1.18HCOOH+H]+. 1H NMR : (400 MHz, CD3OD) :delta 8.52 (br s, 1H), 8.23 (s, 1H), 7.64 (s, 1H), 6.98 (s, 1H), 4.13 (m, 1H), 3.32-3.25 (m, 1H), 2.27 (d, 2H), 2.20 (d, 2H), 1.85-1.65 (m, 2H), 1.60-1.43(m, 2H).

References: [1]Patent: WO2014/11911,2014,A2 .Location in patent: Paragraph 00298; 00299.

5
[ 918340-51-9 ]
[ 64-18-6 ]
trans-4-(dimethylamino)cyclohexan-1-ol [ No CAS ]
[ 1534374-69-0 ]

Yield	Reaction Conditions	Operation in experiment
31%		To a stirred solution of trans-4-(dimethylamino)cyclohexanol in freshly distilled THF (8 mL), cooled to 0C, was slowly added sodium hydride (40 mg, 1.00 mmol, 2.58 equiv, 60% dispersion in mineral oil) under nitrogen. The mixture was stirred at 0C for 30 min and then 4- chlorofuro[2,3-d]pyrimidine (60 mg, 0.39 mmol, 1.00 equiv) was added and the reaction was stirred overnight at 50C. The reaction solution was then quenched by the addition of water, extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (80 mg) was purified by Prep-HPLC with the following conditions (SHIMADZU): Column, SunFire Prep CI 8, 19* 150mm 5um; mobile phase, water with 1% HCOOH and CH3CN (3.0% CH3CN up to 8.0% in 10 min); Flow rate: 20 mL/min; UV detection at 254/220 nm. The product-containing fractions were collected and partially evaporated to remove solvents under reduced pressure. The residue was lyophilized overnight to give the resulted tra/?5-4-(furo[2,3-d]pyrimidin-4-yloxy)-N,N- dimethylcyclohexanamine formate (37.3 mg, 31%) as a white solid. LCMS: (ES, m/z): 262 [M- HCOOH+H]+. 1H NMR: (400 MHz, CD3OD): delta 8.53 (1H, brs), 8.50 (1H, s), 7.84 (1H, d), 6.92 (1H, d), 5.37-5.31 (1H, m), 3.32-3.15 (1H, m), 2.74 (6H, s), 2.45 (2H, d), 2.20 (2H, d), 1.81-1.65 (4H, m).

References: [1]Patent: WO2014/11911,2014,A2 .Location in patent: Paragraph 00302; 00303.

6
[ 918340-51-9 ]
[ 1228947-14-5 ]
[ 1534374-67-8 ]

Yield	Reaction Conditions	Operation in experiment
52%		To a stirred solution of <strong>[1228947-14-5]trans-4-morpholinocyclohexanol</strong> (220 mg, 1.19 mmol, 3.06 equiv) in freshly distilled THF (10 ml), cooled to 0C, was slowly added sodium hydride (65 mg, 1.62 mmol, 4.19 equiv, 60% dispersion in mineral oil) under nitrogen. The mixture was stirred at 0C for 30 min and then 4-chlorofuro[2,3-d]pyrimidine (60 mg, 0.39 mmol, 1.00 equiv) was added and the reaction was stirred overnight at 40C. The reaction was then quenched with water, extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (100 mg) was purified by Prep-HPLC with the following conditions (SHIMADZU): Column, SunFire Prep C I 8, 19* 150mm 5um; mobile phase, water with 1% HCOOH and CH3CN (3.0% CH3CN up to 10.0% in 15 min); Flow rate: 20 mL/min; UV detection at 254/220 nm. The product-containing fractions were collected and partially evaporated to remove solvents under reduced pressure. The residue was lyophilized overnight to give 69.9 mg (52%) of the desired 4-(((trans)-4- morpholinocyclohexyl)oxy)furo[2,3-d]pyrimidine as a white solid. LCMS (ES, m/z): 304 [M+H]+. 1H-NMR: (400 MHz, CD3OD) delta 8.49 (1H, s), 7.82 (1H, d), 6.92 (1H, d), 5.33-5.25 (1H, m), 3.75-3.73 (4H, m), 2.69-2.66 (4H, m), 2.45-2.39 (1H, m), 2.38-2.30 (2H, m), 2.13 (2H, d), 1.67-1.47 (4H, m).

References: [1]Patent: WO2014/11911,2014,A2 .Location in patent: Paragraph 00300; 00301.

7
[ 918340-51-9 ]
3-(3,4-dimethoxybenzyl)-6-(4-hydroxyphenyl)-1,5-dimethylpyrimidine-2,4(1H,3H)-dione [ No CAS ]
6-[4-(furo[2,3-d]pyrimidin-4-yloxy)phenyl]-1,5-dimethylpyrimidine-2,4(1H,3H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%		Step 5. Synthesis of 6-[4-(furo[2,3-d]pyrimidin-4-yloxy)phenyl]-1,5-dimethylpyrimidine- 2,4(1H,3 )-dione (9). The title compound was generated as part of a library using the following protocol: to a 2-dram vial were added C3 (0.13 mmol), C30 (38.2 mg, 0.1 mmol), cesium carbonate (98 mg, 0.3 mmol), di-fe/f-butyl[3,4,5,6-tetramethyl-2',4',6'-tri(propan- 2-yl)biphenyl-2-yl]phosphane (10 mg, 20 muetaiotaomicronIota) and degassed 1 ,4-dioxane (1 mL). The reaction was degassed with nitrogen and shaken and heated at 1 10 C for 20 hours. The reaction mixture was then partitioned between water (1.5 mL) and ethyl acetate (2.5 mL) and filtered through diatomaceous earth; the organic layer was eluted through a solid-phase extraction cartridge charged with sodium sulfate, and the filtrate was concentrated in vacuo. The residue was treated with methoxybenzene (0.1 mL) and trifluoroacetic acid (1.25 mL), and this reaction mixture was shaken and heated at 90 C for 48 hours, whereupon it was concentrated. The residue (35 mg) was purified via reversed phase HPLC (Column: Waters XBridge C18, 5 muetaiota; Mobile phase A: 0.03% ammonium hydroxide in water (v/v); Mobile phase B: 0.03% ammonium hydroxide in acetonitrile (v/v); Gradient: 5% to 100% B). Yield: 2.6 mg, 7.4 muetaiotaomicronIota, 7%. LCMS m/z 351.2 [M+H]+. 1 H NMR (600 MHz, DMSO-d6) delta 8.58 (s, 1 H), 8.18 (d, J=2.4 Hz, 1 H), 7.51 (br AB quartet, JAB=8.7 Hz, DeltanuAlphaBeta=11.1 Hz, 4H), 7.07 (d, J=2.4 Hz, 1 H), 2.94 (s, 3H), 1.56 (s, 3H).

References: [1]Patent: WO2015/162518,2015,A1 .Location in patent: Page/Page column 124.

8
[ 918340-51-9 ]
[ 1609259-55-3 ]
4-[4-(4,6-dimethylpyrimidin-5-yl)-3-methylphenoxy]furo[2,3-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With caesium carbonate; In dimethyl sulfoxide; at 120℃; for 3h;	Step 6. Synthesis of ' 4-[4-{4^-dimethyipynmidin-5-yi)-3-methyiphenoxy]furo[2,3- djpyrimidine (1). To a stirred solution of C3 (33 mg, 0.21 mmol) in dimethyl sulfoxide (1 ml_) was added C5 (45 mg, 0.21 mmol) and cesium carbonate (205 mg, 0.63 mmol). The reaction mixture was stirred at 120 C for 3 hours, then was cooled to room temperature. The reaction mixture was partitioned between ethyl acetate and water, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified via silica gel chromatography (Gradient: 0% to 40% [80:20: 1 dichloromethane / methanol / concentrated ammonium hydroxide] in dichloromethane) to provide the product as a pale yellow solid. Yield: 30 mg, 0.09 mmol, 43%. LCMS m/z 333.1 [M+H]+. 1 H NMR (400 MHz, CDCI3) delta 8.96 (s, 1 H), 8.55 (s, 1 H), 7.76 (d, J=2.3 Hz, 1 H), 7.19 (m, 1 H), 7.10 (m, 1 H), 6.79 (d, J=2.5 Hz, 1 H), 2.24 (s, 6H), 2.03 (s, 3H), 1.51 (s, 3H).

References: [1]Patent: WO2015/162518,2015,A1 .Location in patent: Page/Page column 109.

9
[ 918340-51-9 ]
[ 1609259-39-3 ]
6-[4-(furo[2,3-d]pyrimidin-4-yloxy)-2-methylphenyl]-1,5-dimethylpyrazin-2⁽¹⁾-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With caesium carbonate; In dimethyl sulfoxide; at 120℃; for 3h;	Step 6. Synthesis of 6-[4-(furo[2,3-d]pyrimidin-4-yloxy)-2-methylphenyl]-1 ,5- dimethylpyrazin-2( 1 )-one (3), (-)-6-[4-(furo[2,3-d]py midin-4-yloxy)-2-methylphenyl]- 1,5-dimethylpyrazin-2(1 )-one (4), and (+)-6-[4-(furo[2,3-d]py midin-4-yloxy)-2- methyl phenyl]- 1, 5-dimethylpyrazin-2( 1 )-one (5) . To a stirred solution of C3 (60 mg, 0.39 mmol) in dimethyl sulfoxide (2 mL) was added C17 (121 mg, 0.39 mmol) and cesium carbonate (379 mg, 1.16 mmol). The reaction mixture was stirred at 120 C for 3 hours, cooled to room temperature, and partitioned between ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate, and the combined organic layers were washed sequentially with water and with saturated aqueous sodium chloride solution, then dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified via silica gel chromatography (Gradient: 0% to 30% [80:20: 1 dichloromethane / methanol / concentrated ammonium hydroxide] in dichloromethane) to provide product 3, a mixture of atropenantiomers, as a light yellow foam. Yield: 108 mg, 0.31 mmol, 80%. LCMS m/z 349.1 [M+H]+. 1 H NMR (400 MHz, CDCI3) delta 8.58 (s, 1 H), 8.22 (s, 1 H), 7.72 (d, J=2.5 Hz, 1 H), 7.18-7.35 (m, 3H), 6.91 (d, J=2.4 Hz, 1 H), 3.26 (s, 3H), 2.18 (s, 3H), 2.08 (s, 3H). Compound Example 3 was separated into its atropenantiomers via supercritical fluid chromatography Column: Chiral Technologies Chiralcel OJ-H, 5 muetaiota; Eluent: 3:1 carbon dioxide / 2-propanol). Example 4 [designated the (-)-atropenantiomer according to its observed rotation data] was the first-eluting isomer, followed by Example 5. Example 5 was designated the (+)-atropenantiomer according to its observed rotation data. 4: LCMS m/z 349.1 [M+H]+. 1 H NMR (400 MHz, CD3OD) delta 8.49 (s, 1 H), 8.11 (s, 1 H), 7.96 (d, J=2.5 Hz, 1 H), 7.36-7.41 (m, 2H), 7.33 (br dd, half of ABX pattern, J=8, 2 Hz, 1 H), 7.00 (d, J=2.5 Hz, 1 H), 3.27 (s, 3H), 2.18 (s, 3H), 2.06 (s, 3H). 5: LCMS m/z 349.1 [M+H]+. 1 H NMR (400 MHz, CD3OD) delta 8.49 (s, 1 H), 8.11 (s, 1 H), 7.96 (d, J=2.5 Hz, 1 H), 7.36-7.41 (m, 2H), 7.33 (br dd, half of ABX pattern, J=8, 2 Hz, 1 H), 7.00 (d, J=2.5 Hz, 1 H), 3.27 (s, 3H), 2.18 (s, 3H), 2.06 (s, 3H).

References: [1]Patent: WO2015/162518,2015,A1 .Location in patent: Page/Page column 115-116.

10
[ 918340-51-9 ]
[ 1609259-51-9 ]
5-(4-(furo[2,3-d]pyrimidin-4-yloxy)-2-methylphenyl)-4,6-dimethyl-2-(tetrahydro-2H-pyran-2-yl)pyridazin-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In dimethyl sulfoxide; at 120℃; for 6h;	Step 9. Synthesis of 5-(4-(furo[2,3-d]pyrimidin-4-yloxy)-2-methylphenyl)-4, 6-dimethyl-2- (tetrahydro-2H-pyran-2-yl)pyridazin-3(2H)-one (C26). To a resealable pressure tube were added C3 (38.9 mg, 0.25 mmol), C25 (66 mg, 0.21 mmol), cesium carbonate (205 mg, 0.63 mmol) and dimethyl sulfoxide (15 ml_). The reaction mixture was heated to 120 C for 6 hours, then cooled to room temperature and diluted with ethyl acetate. The mixture was washed sequentially with water and with saturated aqueous sodium chloride solution, then dried over magnesium sulfate. The solvent was removed in vacuo and the residue was used in the next step without further purification. LCMS m/z 433.1 [M+H]+.

References: [1]Patent: WO2015/162518,2015,A1 .Location in patent: Page/Page column 120-121.

11
[ 918340-51-9 ]
[ 1609259-51-9 ]
5-[4-(furo[2,3-d]pyrimidin-4-yloxy)-2-methylphenyl]-4,6-dimethylpyridazin-3(2 )-one [ No CAS ]

References: [1]Patent: WO2015/162518,2015,A1 .

12
[ 139370-56-2 ]
[ 918340-51-9 ]

References: [1]Patent: WO2015/162518,2015,A1 .

13
[ 918340-51-9 ]
[ 367-27-1 ]
[ 1613479-37-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3199 - 3203.

14
Furo[2,3-d]pyrimidin-4(3H)-one [ No CAS ]
[ 918340-51-9 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In acetonitrile; at 110℃; for 0.0833333h;Microwave irradiation;	General procedure: A solution of 6,7-dimethoxyisoquinolin-1(2H)-one(200 mg, 0.97 mmol), phosphoryl trichloride (0.268 mL, 2.92 mmol) inacetonitrile (5 mL) was stirred at 110 C for 5 minutes under microwaveirradiation. The reaction was quenched with a saturated aqueous sodium bicarbonatesolution and stirred at ambient temperature for 1 h. It was filtered throughcelite and washed with ethyl acetate. The filtrate was concentrated to dryness.The crude material was purified by flash chromatography, eluting with heptanesand ethyl acetate (1:0 to 0:1) to give the desired product as a gum (99 mg,45.4 %).

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3199 - 3203.

15
[ 918340-51-9 ]
[ 1308400-20-5 ]
4-(furo[2,3-d]pyrimidin-4-ylamino)-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrazole-3-carboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 1499 - 1518.

16
[ 918340-51-9 ]
4-chloro-6-iodofuro[2,3-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 49A 4-chloro-6-iodofuro[2,3-d]pyrimidine To a mixture of <strong>[918340-51-9]4-chlorofuro[2,3-d]pyrimidine</strong> (1 g) in tetrahydrofuran (30.8 mL) at -78 C. was added lithium diisopropylamide (1 M in tetrahydrofuran/hexane, 7.1 mL) over -5 minutes, and the mixture was allowed to stir at -78 C. for 1 hour. A mixture of iodine (1.8 g) in tetrahydrofuran (15.4 mL) was added over 10 minutes, and the reaction mixture was allowed to stir. The cooling bath was removed after 15 minutes, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 10% sodium thiosulfate mixture, cooled to 0 C., and stirred for 1 hour. The mixture was filtered, and the material was washed with water and pentane and dried under vacuum to provide the title compound. MS(ESI) m/z 281.0 (M+H)+.

References: [1]Patent: US2019/55264,2019,A1 .Location in patent: Paragraph 0708.

17
[ 918340-51-9 ]
5-bromo-4-chlorofuro[2,3-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 138A 5-bromo-<strong>[918340-51-9]4-chlorofuro[2,3-d]pyrimidine</strong> 4-Chlorofuro[2,3-d]pyrimidine (4 g) was dissolved in chloroform (15 mL). Acetic acid (1.63 mL) was added followed by bromine (4.00 mL). The reaction mixture was stirred for 16 hours at 25 C. The reaction mixture was diluted with additional chloroform (35 mL) and was cooled to 5 C. 1,8-Diazabicyclo[5.4.0]undec-7-ene (12 mL) was added. The reaction mixture was allowed to warm up to 25 C. and was stirred for a further 30 minutes. The reaction mixture was cooled to 5 C. and water (100 mL) was added. The mixture was extracted with dichloromethane (2*200 mL). The combined organic layers were washed with water and aqueous sodium thiosulfate solution, dried over MgSO4, filtered, and concentrated in vacuo. The residue obtained was purified by silica gel flash chromatography (80 g Chromabond column, gradient ethyl acetate in heptane 0-30%). The residue was dissolved in dichloromethane (20 mL), and pentane (80 mL) was added. The precipitated material was filtered off, washed with pentane and dried to give the title compound. MS (ESI) m/z 232.9/234.9 (M+H)+.

References: [1]Patent: US2019/55264,2019,A1 .Location in patent: Paragraph 1186.

18
[ 918340-51-9 ]
6-bromo-4-chloro-5-(3-chloro-2-methyl-4-((triisopropylsilyl)oxy)phenyl)furo[2,3-d]pyrimidine [ No CAS ]