1-(Bromomethyl)-2,3-difluoro-benzene → 2-[[(2,3-Difluorophenyl)methyl]thio]-4,6-pyrimidinediamine

HRID 497727Notes

Reaction equation

HRID 497727 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([SH:9])[N:3]=1.CC(C)([O-])C.[K+].[F:16][C:17]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Br>CS(C)=O>[F:16][C:17]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][S:9][C:4]1[N:5]=[C:6]([NH2:8])[CH:7]=[C:2]([NH2:1])[N:3]=1

Participants

5

Reactant 3

HCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 23665647Potassium tert-butoxideHCID 1785079174,6-diaminopyrimidine-2-thiol

Product 1

HCID 174102292-[[(2,3-Difluorophenyl)methyl]thio]-4,6-pyrimidinediamineYield 94.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4,6-diamino-2-pyrimidinethiol (7.3 g) was dissolved in DMSO (100 ml) at room temperature under an atmosphere of nitrogen. Potassium tert-butoxide (1M in THF, 48.3 ml) was added followed by 2,3-difluorobenzyl-bromide (10.0 g). The mixture was stirred for 2 hours at room temperature. The reaction mixture was then partitioned between ethyl acetate and ammonium chloride. The organic phase was washed with ammonium chloride (3×) and brine, then dried over magnesium sulphate and evaporated to give the subtitled product as a white solid (12.2 g)

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and ammonium chloride
  2. washThe organic phase was washed with ammonium chloride (3×) and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-8849eac37abf41b5a6d4a3d4f57259ea
Source dataset
uspto-grants-2005_09
Patent number
US06949643B2

Reaction notes

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