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

HRID 1097362
Notes
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Reaction equation

HRID 1097362 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-de9bc9e5a71542a096516265ea9d7e49
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08143261B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes