Hydrochloric Acid → 7-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-2(3H)-one

HRID 1006509Notes

Reaction equation

HRID 1006509 reaction equation
[Cl:1][C:2]1[C:3]2[S:20][C:19]([O:21]C)=[N:18][C:4]=2[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=2[F:17])[N:7]=1.Cl.O>O1CCOCC1>[Cl:1][C:2]1[C:3]2[S:20][C:19](=[O:21])[NH:18][C:4]=2[N:5]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=2[F:17])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 226713137-Chloro-5-[(2,3-difluorophenylmethyl)thio]-2-methoxythiazolo[4,5-d]pyrimidine

Product 1

HCID 226713277-Chloro-5-[[(2,3-difluorophenyl)methyl]thio]thiazolo[4,5-d]pyrimidin-2(3H)-oneYield 72.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

The product from example 31 step (b) (2.0 g) was dissolved in dioxan (150 ml) followed by addition of concentrated hydrochloric acid (1 ml) and water (1 ml) and the whole heated at 40° C. for 67 hours. The mixture was evaporated to dryness and purified by column chromatography (silica-dichloromethane) to give a white solid (1.4 g).

Workup

  1. customThe mixture was evaporated to dryness
  2. custompurified by column chromatography (silica-dichloromethane)

Sources & evidence

ORD record
ord-59463f052649474cbd8173086eec046f
Source dataset
uspto-grants-2004_09
Patent number
US06790850B1

Reaction notes

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