Methanol → 7-Chloro-5-[(2,3-difluorophenylmethyl)thio]-2-methoxythiazolo[4,5-d]pyrimidine

HRID 1097361Notes

Reaction equation

HRID 1097361 reaction equation
Br[C:2]1[S:3][C:4]2[C:9]([Cl:10])=[N:8][C:7]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=3[F:20])=[N:6][C:5]=2[N:21]=1.[OH-:22].[K+].[CH3:24]O>Cl>[Cl:10][C:9]1[C:4]2[S:3][C:2]([O:22][CH3:24])=[N:21][C:5]=2[N:6]=[C:7]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[N:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 226713342-Bromo-7-chloro-5-((2,3-difluorobenzyl)thio)thiazolo[4,5-d]pyrimidine

Product 1

HCID 226713137-Chloro-5-[(2,3-difluorophenylmethyl)thio]-2-methoxythiazolo[4,5-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

The product of example 31 step a) (5.6 g) was suspended in methanol (150 ml) and potassium hydroxide powder (0.77 g) added. The whole was stirred at room temperature for 2 hours. The mixture was adjusted to pH 7 with a few drops of concentrated hydrochloric acid before it was evaporated to dryness. Purified by column chromatography (silica—3:2 to 1:1 isohexane/dichloromethane) to give white solid (2.0 g).

Workup

  1. customwas evaporated to dryness
  2. customPurified by column chromatography (silica—3:2 to 1:1 isohexane/dichloromethane)

Sources & evidence

ORD record
ord-74c6680aa43d45aeb301dda4bd5924aa
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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