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

HRID 1789942Notes

Reaction equation

HRID 1789942 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].[Cl:13][C:14]1[C:15]([F:22])=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.O>CO>[Cl:13][C:14]1[C:15]([F:22])=[C:16]([CH2:17][S:11][C:7]2[N:8]=[C:9]([NH2:10])[C:4]([NH2:3])=[C:5]([S:12][CH2:17][C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([Cl:13])[C:15]=3[F:22])[N:6]=2)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 5228271-(Bromomethyl)-3-chloro-2-fluorobenzeneHCID 178509065HCID 178509065, compound

Product 1

HCID 220370332,6-Bis[[(3-chloro-2-fluorophenyl)methyl]thio]-4,5-pyrimidinediamineYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of potassium hydroxide powder (2.5 g) in methanol (80 ml) was added first 5,6-diamino-2,4-pyrimidinedithiol (3.6 g) followed by 3-chloro-2-fluorobenzyl bromide (6.3 g). The reaction mixture was stirred for one hour at room temperature then poured into water (180 ml), giving a brown precipitate. This was isolated by filtration, washing with isopropyl alcohol and diethyl ether, to give the subtitled compound as a pale brown solid (5.4 g).

Workup

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

Sources & evidence

ORD record
ord-a8c82af914864d3bb1fb466e1bacd794
Source dataset
uspto-grants-2006_07
Patent number
US07071193B2

Reaction notes

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