Sodium Hydroxide → HCID 56646340, compound

HRID 1773602Notes

Reaction equation

C([Si](C)(C)[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[NH:21][C:22]([C:24]2[CH:25]=[N:26][N:27]3[C:32]([CH3:33])=[CH:31][CH:30]=[N:29][C:28]=23)=[O:23])[CH2:9][CH2:8]1)(C)(C)C.[OH-].[Na+]>Cl.CO>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH:10]2[CH2:11][CH2:12][CH:7]([OH:6])[CH2:8][CH2:9]2)=[C:15]([NH:21][C:22]([C:24]2[CH:25]=[N:26][N:27]3[C:32]([CH3:33])=[CH:31][CH:30]=[N:29][C:28]=23)=[O:23])[CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrochloric acid (concentrated, 5 drops) was added to a solution of 7-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid {2-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-5-chloro-phenyl}-amide (ca. 0.22 mmol) in methanol (3 mL) and the resulting mixture was heated at 80° C. for 30 minutes. The resulting mixture was cooled, basified by addition of an aqueous solution of sodium hydroxide (4 M, few drops) and evaporated under reduced pressure. The crude residue was purified by flash chromatography to give 28 mg of 7-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-chloro-2-(4-hydroxy-cyclohexyloxy)-phenyl]-amide (off-white solid). MS=401 [M+H]+.

Workup

temperatureThe resulting mixture was cooled
customevaporated under reduced pressure
customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record: ord-b9221475925445e1bec0cfead488aede
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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