Water → 2,6-Bis[[(2,3-difluorophenyl)methyl]thio]-4,5-pyrimidinediamine

HRID 1789935Notes

Reaction equation

HRID 1789935 reaction equation
[OH-].[K+].[NH2:3][C:4]1[C:5]([SH:12])=[N:6][C:7]([SH:11])=[N:8][C:9]=1[NH2:10].[F:13][C:14]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br.O>CO>[F:13][C:14]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][S:11][C:7]1[N:8]=[C:9]([NH2:10])[C:4]([NH2:3])=[C:5]([S:12][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:14]=2[F:13])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 178509065HCID 178509065, compound

Product 1

HCID 220370522,6-Bis[[(2,3-difluorophenyl)methyl]thio]-4,5-pyrimidinediamineYield 64.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of potassium hydroxide powder (7.72 g) in methanol (250 ml) was added first 5,6-diamino-2,4-pyrimidinedithiol (10.9 g) followed by 2,3-difluorobenzyl bromide (22.5 g). The reaction mixture was stirred for one hour at room temperature then poured into water (500 ml), giving a brown precipitate. This was isolated by filtration, washing with isopropanol and diethyl ether, to give the subtitled compound as a pale brown solid (15.0 g).

Workup

  1. customgiving a brown precipitate
  2. customThis was isolated by filtration
  3. washwashing with isopropanol and diethyl ether

Sources & evidence

ORD record
ord-35a49464e9924d568c49d65afdf8ac83
Source dataset
uspto-grants-2006_07
Patent number
US07071193B2

Reaction notes

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