Lithium Hydroxide → HCID 66847716, compound

HRID 1631296Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]([O:25]CC)=[O:24])=[C:16]2[N:15]=1.[Li+].[OH-]>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[C:16]2[N:15]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(R)-ethyl 5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (2.13 g, 5.72 mmol) was suspended in EtOH (28.6 mL) and heated at 90° C. for 20 min (homogeneous). 1M aq. LiOH (11.4 mL, 11.4 mmol) was added and the reaction mixture was heated for 15 hours at 90° C. After cooling, the reaction mixture was concentrated, diluted with water and washed with EtOAc to remove any unreacted starting material. The aqueous layer was then acidified to pH 1 using 2N HCl. After extracting with DCM and EtOAc, the combined organic fractions were dried with MgSO4, filtered and concentrated to afford (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (1.82 g, 92.4%) as a light yellow solid. MS (apci) m/z=345.0 (M+H).

Workup

temperaturethe reaction mixture was heated for 15 hours at 90° C
temperatureAfter cooling
concentrationthe reaction mixture was concentrated
additiondiluted with water
washwashed with EtOAc
customto remove
extractionAfter extracting with DCM and EtOAc
dry with materialthe combined organic fractions were dried with MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-2b6cf0c5f0854350a9333a030923937e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791123B2

Reaction notes

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