Sodium hydride → 6-Amino-2-{[(2,3-difluorophenyl)methyl]sulfanyl}pyrimidin-4(1H)-one

HRID 731525Notes

Reaction equation

HRID 731525 reaction equation
O.[NH2:2][C:3]1[CH:8]=[C:7]([OH:9])[N:6]=[C:5]([SH:10])[N:4]=1.[H-].[Na+].[F:13][C:14]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br>CN(C)C=O>[NH2:2][C:3]1[N:4]=[C:5]([S:10][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:14]=2[F:13])[NH:6][C:7](=[O:9])[CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 178507962HCID 178507962, compound

Product 1

HCID 1359667216-Amino-2-{[(2,3-difluorophenyl)methyl]sulfanyl}pyrimidin-4(1H)-oneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Amino-6-hydroxy-2-mercaptopyrimidine monohydrate (7.1 g) was added portion wise to a stirred suspension of 60% sodium hydride (2.4 g) in dry N,N-dimethylformamide (70 ml). After 1 hour a solution of 2,3-Difluorobenzyl bromide (10 g) in dry N,N-dimethylformamide (10 ml) was added. Stirred over weekend at room temperature. Poured on to ice/water and the precipitate was collected by filtration to give 9.6 g of product. 81% yield.

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a939c13c6f27424abbbd485911d8cefe
Source dataset
uspto-grants-2009_09
Patent number
US07585867B2

Reaction notes

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