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

HRID 1006508Notes

Reaction equation

HRID 1006508 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-9414865e4b8044c0a4fe600fec071c31
Source dataset
uspto-grants-2004_09
Patent number
US06790850B1

Reaction notes

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