Water → 4-amino-2-[[(2,3-difluorophenyl)methyl]thio]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 968223

Reaction equation

HRID 968223 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]2[CH2:13][C:12](=[O:14])[NH:11][C:6]=2[N:7]=[C:8]([SH:10])[N:9]=1.[F:15][C:16]1[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Br.O>CN(C=O)C>[NH2:3][C:4]1[C:5]2[CH2:13][C:12](=[O:14])[NH:11][C:6]=2[N:7]=[C:8]([S:10][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:16]=2[F:15])[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 178509058HCID 178509058, compound

Product 1

HCID 697498014-amino-2-[[(2,3-difluorophenyl)methyl]thio]-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (125 mg) in dry DMF (5 ml) was added a solution of the product from example 3, step (a) (0.57 g) in DMF (10 ml). The mixture was allowed to stir for 30 mins. To the solution was added 2,3-difluorobenzyl bromide (0.39 ml) and the mixture stirred for 2 hours. Poured into water and the crude product extracted into ethyl acetate. Chromatography on silica eluting with 10% ethyl acetate/dichloromethane afforded the title compound (0.35 g).

Workup

  1. stirringthe mixture stirred for 2 hours
  2. extractionthe crude product extracted into ethyl acetate

Sources & evidence

ORD record
ord-f957c8ebbbea45f7b458ac56438a566c
Source dataset
uspto-grants-2005_10
Patent number
US06958344B2

Linked notes

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