83410-37-1|5-Iodo-2,6-dimethylpyrimidin-4-ol| Ambeed

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Quality Control of [ 83410-37-1 ] Purity: 95+% SDS Specification

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Product Details of [ 83410-37-1 ]

CAS No. :	83410-37-1
Formula :	C₆H₇IN₂O
M.W :	250.04
SMILES Code :	OC1=NC(C)=NC(C)=C1I
MDL No. :	MFCD02081996
InChI Key :	LLRCHCURQABDLS-UHFFFAOYSA-N
Pubchem ID :	135447935

Safety of [ 83410-37-1 ]

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

Application In Synthesis of [ 83410-37-1 ]

* 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 [ 83410-37-1 ]

[ 83410-37-1 ] Synthesis Path-Downstream 1~35

1
[ 6622-92-0 ]
[ 83410-37-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With iodine; sodium hydroxide; In water; at 80℃; for 2.0h;	Step A: 2,6-Dimethylpyrimidin-4-ol (5.0 g, 40 mmol) was dissolved in aqueous NaOH solution (50 mL, 1 M, 50 mmol). To the solution was added iodine (10.2 g, 40 mmol). The mixture was gradually heated to 80 C. and stirred for 2 h. After cooling the mixture to room temperature, acetic acid was added to adjust the pH ?6. A precipitate formed and was collected by filtration. The solid was washed with water and dried to give 5-iodo-2,6-dimethylpyrimidin-4-ol (6.51 g, 65%). MS m/z 251.2 [M+H]+.
50.5 g (50%)	With sodium hydroxide; iodine;	Step 1 2,6-Dimethyl-5-iodo-4-hydroxypyrimidine A mechanically stirred mixture of 2,6-dimethyl-4-hydroxypyrimidine (50.0 g, 0.403 mol), iodine (102.2 g, 0.403 mol), and 1N NaOH (503 mL) was heated under reflux for 2 h. The mixture was extracted with CHCl3 (some product fell out of solution and was collected by filtration: 24.5 g). The extracts were dried MgSO4) and concentrated to give 40.9 g of an orange solid which contained starting material and product. Trituration with EtOAc gave 26.0 g of product. The total yield of product was 50.5 g (50%), mp 208-210 (dec). An analytical sample was recrystallized from EtOH, mp 216-218. 1 H NMR (DMSO-d6) delta2.21 (s, 3H), 2.39 (s, 3H), 12.58 (br s, 1H). Anal. calcd for C6 H7 IN2 O: C, 28.82; H, 2.82; N, 11.20; Found: C, 28.85; H, 2.76; N, 10.98.
	With iodine; sodium hydroxide; In water; at 120℃; for 2.0h;	(2) 5-iodo-2,6-dimethylpyrimidin-4-ol (326-2)The crude compound 326-1 (25.6 g) was dissolved in a 1.25 N sodium hydroxide aqueous solution (140 ml). Iodine (19.9 g) was added to the solution, and the obtained mixture was then stirred at 120 C. for 2 hours. The temperature of the reaction solution was returned to room temperature, and the reaction solution was then extracted with chloroform. The obtained organic layer was dried over magnesium sulfate and then concentrated under reduced pressure, so as to obtain the title compound (14.5 g).1H-NMR (400 MHz, CDCl3) delta (ppm): 2.49 (s, 3H), 2.60 (s, 3H), 12.8 (brs, 1H)

References: [1]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 398.
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 4251 - 4260.
[3]Tetrahedron,2007,vol. 63,p. 1931 - 1936.
[4]Patent: US5466692,1995,A .
[5]Patent: US2012/95031,2012,A1 .Location in patent: Page/Page column 160.

2
[ 83410-37-1 ]
[ 83410-16-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With trichlorophosphate; at 110℃; for 2.0h;	Step B: 5-Iodo-2,6-dimethylpyrimidin-4-ol (4.6 g, 18.4 mmol) was combined with phosphorus oxychloride (15 mL). The mixture was stirred at 110 C. for 2 h, then the solvent was removed under vacuum. The residue was dissolved in CH2Cl2 and washed with an aqueous saturated NaHCO3 solution and brine. The organic layer was concentrated and purified by silica gel column chromatography (0-10% EtOAc in CH2Cl2) to give the title compound (3.86 g, 78%) as colorless oil that solidified on standing. MS m/z 269.2 [M+H]+.
33.8 g (62%)	With trichlorophosphate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; toluene;	Step 2 4-Chloro-2,6-dimethyl-5-iodopyrimidine A mixture of <strong>[83410-37-1]2,6-dimethyl-5-iodo-4-hydroxypyrimidine</strong> (24.5 g, 0.098 mol), phosphorus oxychloride (30.0 g, 0.196 mol) and toluene (200 mL) was heated under reflux for 1 h. The mixture was concentrated and ice water (100 mL) was added. The pH was adjusted to 5 with 2.5N NaOH and the mixture was extracted with CH2 Cl2. The combined extracts were washed with brine, dried MgSO4), and concentrated to give 24.6 g of a brown solid. The crude product was combined with 26.0 g of similarly prepared material and filtered through a short column of silica gel eluted with CH2 Cl2 to give 33.8 g (62%) of product as a yellow solid. An analytical sample was recrystallized from hexane/CH2 Cl2, mp 62-64 C. 1 H NMR (CDCl3) delta2.61 (s, 3H), 2.73 (s, 2H). Anal. calcd for C6 H6 ClIN2: C, 26.84; H, 2.26; N, 10.44; Found: C, 27.04; H, 2.15; N, 10.14.
		4-Chloro-5-iodo-2,6-dimethylpyrimidine (9); <n="32"/>[0096] To a solution of 1 g (4 mmol, leq.) of <strong>[83410-37-1]5-iodo-2,6-dimethylpyrimidin-4-ol</strong> (8) in 10 mL of toluene was added 1.21 g (8 mmol, 2 eq.) of POCl3 and the mixture was heated at reflux for 1 h. The mixture was concentrated and ice water was added. The pH was adjusted to 5 with 2.5 N NaOH and extracted with CH2Cl2. The combined extracts were washed with brine, dried (Na2SO4) and the solvent removed in vacuo. Then the crude product was purified by flash chromatography to provide 4-chloro-5-iodo-2,6-dimethylpyrimidine (9).

References: [1]Patent: US9617268,2017,B2 .Location in patent: Page/Page column 398.
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 4251 - 4260.
[3]Patent: US5466692,1995,A .
[4]Patent: WO2009/155448,2009,A1 .Location in patent: Page/Page column 29-30.

3
[ 2561-17-3 ]
[ 83410-37-1 ]
[ 929880-38-6 ]