135292-35-2|2-Chloro-4-methoxy-5-methylpyrimidine| Ambeed

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Quality Control of [ 135292-35-2 ] Purity: 95% SDS Specification

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Product Details of [ 135292-35-2 ]

CAS No. :	135292-35-2
Formula :	C₆H₇ClN₂O
M.W :	158.59
SMILES Code :	CC1=CN=C(Cl)N=C1OC
MDL No. :	MFCD20483333
InChI Key :	RCJNDDNXUYCUOY-UHFFFAOYSA-N
Pubchem ID :	11051933

Safety of [ 135292-35-2 ]

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

Application In Synthesis of [ 135292-35-2 ]

* 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.

Downstream synthetic route of [ 135292-35-2 ]

[ 135292-35-2 ] Synthesis Path-Downstream 1~25

1
[ 135292-35-2 ]
[ 135292-31-8 ]
[ 135292-37-4 ]

References: [1]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 657 - 665.

2
[ 135292-35-2 ]
phenyl 2,3-dideoxy-1-thio-D-glycero-pentofuranoside [ No CAS ]
phenyl 2,3-dideoxy-5-O-(4-methoxy-5-methyl-2-pyrimidyl)-1-thio-D-glycero-pentofuranoside [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

3
[ 135292-35-2 ]
((2R,3S,5R)-3-Fluoro-5-phenylsulfanyl-tetrahydro-furan-2-yl)-methanol [ No CAS ]
[ 155446-91-6 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

4
[ 135292-35-2 ]
((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-yl)-methanol [ No CAS ]
[ 155446-90-5 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

5
[ 135292-35-2 ]
((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-yl)-methanol [ No CAS ]
[ 155446-90-5 ]
4-Methoxy-5-methyl-2-((2S,5R)-5-phenylsulfanyl-2,5-dihydro-furan-2-ylmethoxy)-pyrimidine [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1994,p. 2541 - 2542.

6
[ 135292-35-2 ]
[ 204636-93-1 ]
4-Methoxy-5-methyl-2-((S)-5-phenylselanyl-tetrahydro-furan-2-ylmethoxy)-pyrimidine [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 1807 - 1810.

7
[ 135292-35-2 ]
[ 220222-88-8 ]
[ 220222-89-9 ]

References: [1]Heterocycles,1999,vol. 50,p. 21 - 26.

8
[ 135292-35-2 ]
1-((2S,3R)-2-Hydroxymethyl-2,3-dihydro-furan-3-yl)-4-methoxy-5-methyl-1H-pyrimidin-2-one [ No CAS ]

References: [1]Journal of the Chemical Society. Chemical communications,1994,p. 2541 - 2542.

9
[ 135292-35-2 ]
[ 3416-05-5 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

10
[ 135292-35-2 ]
[ 30516-87-1 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

11
[ 135292-35-2 ]
[ 155446-85-8 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

12
[ 135292-35-2 ]
(S)-5-(4-Methoxy-5-methyl-pyrimidin-2-yloxymethyl)-tetrahydro-furan-2-ol [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

13
[ 135292-35-2 ]
[ 145688-92-2 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

14
[ 135292-35-2 ]
[ 108441-68-5 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

15
[ 135292-35-2 ]
C₁₁H₁₅N₂O₃⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

16
[ 135292-35-2 ]
C₁₁H₁₄FN₂O₃⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

17
[ 135292-35-2 ]
C₁₁H₁₄N₅O₃⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

18
[ 135292-35-2 ]
[ 25526-93-6 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 1883 - 1886.

Yield	Reaction Conditions	Operation in experiment
100%		General procedure: title compound (81%) as an orange solid, which was used without further purification.LRMS (m/z): 163 (M+1)+.1H-NMR δ (CDCl3): 4.11 (s, 3H), 8.20 (d, 1 H)
85%	With sodium; at 20.0℃;	General procedure: sodium (450 mg, 19 mmol) in methanol (20 mL) was added a solution of 2,4-dichloro-5-fluoropyrimidine (3.25 g, 19 mmol) in methanol (10mL). The reaction mixture was stirred at room temperature overnight before being partitioned between water and diethyl ether. The organic phase was separated, washed with brine and evaporated to dryness to give the title compound as an orange oil (80%), which was used in the next step without further purification.1H-NMR δ (400 MHz, CDCl3): 4.11 (s, 3H), 8.20 (s, 1 H).

20
[ 67-56-1 ]
[ 1780-31-0 ]
[ 124-41-4 ]
[ 135292-35-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	at 20.0℃; for 12.0h;	To a solution of 2,4-dichloro-5-methylpyrimidine (12.8 g, 80 mmol, 1 equiv) in MeOH (30 mL) was added NaOMe (5 mol/L in MeOH, 14.8 mL, 74 mmol, 0.9 equiv) dropwise. The reaction mixture was stirred at room temperature for 12 hours and concentrated. The residue was charged with H2O (30 mL) and extracted with DCM (3 * 80 mL). The combined organic phase were washed with brine (30 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluted with PE/EtOAc = 100/1) to afford the title compound 2-chloro-4- methoxy-5-methylpyrimidine as a white solid (9.3 g, 74% yield). LC-MS: m/z 159.1 (M+H)+.
62%	for 20.0h;	5.4M Sodium methoxide in MeOH (1.14 mL) was added to a suspension of 2,4-dichloro-5-methylpyrimidine (1.0 g, 6.1 mmol) in MeOH (20 mL) and the reaction stirred for 20 h. The mixture was concentrated and the residue partitioned between EtOAc and water. The aqueous layer was extracted into EtOAc (x3), the combined organics washed with brine, dried (MgSO4) and concentrated. The residue was purified by Biotage Isolera chromatography (silica gel, eluting with 0-50% EtOAc in heptane to yield 600 mg (62% yield) of the title compound as a white solid. 1H NMR (500 MHz, CDCl3) d 8.10 (s, 1H), 4.03 (s, 3H), 2.12 (d, J = 0.7 Hz, 3H). LCMS (Analytical Method D) Rt= 1.00, MS (ESIpos): m/z= 158.9 [M+H]+.

References: [1]Patent: WO2019/169193,2019,A1 .Location in patent: Page/Page column 108.
[2]Patent: WO2020/97609,2020,A1 .Location in patent: Page/Page column 201.

21
[ 67-56-1 ]
[ 201230-82-2 ]
[ 135292-35-2 ]
methyl 4-methoxy-5-methylpyrimidine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; In N,N-dimethyl-formamide; at 120.0℃; under 2585.81 Torr; for 48.0h;	To a solution of <strong>[135292-35-2]2-chloro-4-methoxy-5-methylpyrimidine</strong> (9.3 g, 58.6 mmol, 1 equiv) in MeOH (220 mL) and DMF (45 mL) were added Pd(dppf)Cl2 (2.1 g, 2.9 mmol, 0.05 equiv) and triethylamine (17.8 g, 175.8 mmol, 3 equiv). The mixture was degassed and refilled with CO three times and then stirred at l20C under CO (50 Psi) for 48 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel chromatography (eluted with PE/EtOAc = 10/1) to afford the title compound methyl 6-(trifluoromethoxy)picolinate as yellow oil (5.0 g, 47% yield). LC-MS : m/z 183.1 (M+H) +

References: [1]Patent: WO2019/169193,2019,A1 .Location in patent: Page/Page column 108-109.

22
[ 135292-35-2 ]
4-methoxy-5-methylpyrimidine-2-carboxylic acid [ No CAS ]

References: [1]Patent: WO2019/169193,2019,A1 .

23
[ 135292-35-2 ]
2‐hydrazinyl‐4‐methoxy‐5‐methylpyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With hydrazine hydrate; In ethanol; at 60.0℃; for 4.0h;	Hydrazine hydrate (768 µL, 15.8 mmol) was added to a solution of 2- chloro-4-methoxy-5-methylpyrimidine (250 mg, 1.6 mmol) (Intermediate 87) in EtOH (4 mL) and the reaction heated to 60 C for 4 h. The reaction was cooled and allowed to stand at room temperature for 18 h. The solid material was collected by filtration, washed with EtOH and dried affording 110 mg (34% yield) of the title compound as a white solid. LCMS (Analytical Method D) Rt= solvent front, MS (ESIpos): m/z= 154.90 [M+H]+.

References: [1]Patent: WO2020/97609,2020,A1 .Location in patent: Page/Page column 201.

24
[ 135292-35-2 ]
7‐methoxy‐6‐methyl‐2H,3H‐[1,2,4]triazolo[4,3‐a]pyrimidin‐3‐one [ No CAS ]

References: [1]Patent: WO2020/97609,2020,A1 .

25
(R)-6-amino-4-isopropyl-1,3-dimethyl-3,4-dihydroquinoxalin-2(1H)-one [ No CAS ]
[ 135292-35-2 ]
C₁₉H₂₅N₅O₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 9787 - 9802.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Ethers • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 135292-35-2 ]

Chlorides

A580720 [135292-36-3]

2-Chloro-4-ethoxy-5-methylpyrimidine

Similarity: 0.94

A174023 [1106295-93-5]

2-Chloro-4-methoxypyrimidine-5-carbonitrile

Similarity: 0.89

A521491 [142451-96-5]

2-Chloro-4-methoxypyrimidine-5-carbaldehyde

Similarity: 0.89

A426344 [477723-08-3]

2-Chloro-4-ethoxypyrimidine-5-carbonitrile

Similarity: 0.84

A770667 [1312535-76-4]

2-Chloro-4-methoxy-5-(trifluoromethyl)pyrimidine

Similarity: 0.83

Ethers

A580720 [135292-36-3]

2-Chloro-4-ethoxy-5-methylpyrimidine

Similarity: 0.94

A174023 [1106295-93-5]

2-Chloro-4-methoxypyrimidine-5-carbonitrile

Similarity: 0.89

A521491 [142451-96-5]

2-Chloro-4-methoxypyrimidine-5-carbaldehyde

Similarity: 0.89

A738700 [17758-12-2]

4-Methoxy-5-methylpyrimidine

Similarity: 0.86

A426344 [477723-08-3]

2-Chloro-4-ethoxypyrimidine-5-carbonitrile

Similarity: 0.84

Related Parent Nucleus of
[ 135292-35-2 ]

Pyrimidines

A580720 [135292-36-3]

2-Chloro-4-ethoxy-5-methylpyrimidine

Similarity: 0.94

A174023 [1106295-93-5]

2-Chloro-4-methoxypyrimidine-5-carbonitrile

Similarity: 0.89

A521491 [142451-96-5]

2-Chloro-4-methoxypyrimidine-5-carbaldehyde

Similarity: 0.89

A738700 [17758-12-2]

4-Methoxy-5-methylpyrimidine

Similarity: 0.86

A426344 [477723-08-3]

2-Chloro-4-ethoxypyrimidine-5-carbonitrile

Similarity: 0.84

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CAS No.: 135292-35-2

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