Sodium borohydride → HCID 86691736, compound

HRID 1426947Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]2[CH:30]=[CH:29][N:28]3[N:31]=[CH:32][C:33]([CH:34]=[O:35])=[C:27]3[N:26]=2)[CH:3]=1.[BH4-].[Na+]>CO.[Cl-].[Na+].O>[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[C:4]([C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]2[CH:30]=[CH:29][N:28]3[N:31]=[CH:32][C:33]([CH2:34][OH:35])=[C:27]3[N:26]=2)[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (R)-tert-butyl 3-(4-fluoro-2-(1-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)phenoxy)propylcarbamate (85.0 mg, 0.176 mmol) in MeOH (2 mL) was first cooled to 0° C., then NaBH4 (4.04 mg, 0.176 mmol) was introduced, and the reaction was stirred at 0° C. for 1 hour. The reaction was diluted with brine and extracted with DCM in a phase separator cartridge. The combined organic extracts were concentrated to provide (R)-tert-butyl 3-(4-fluoro-2-(1-(3-(hydroxymethyl)pyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)phenoxy)propylcarbamate (86 mg, 101% yield) as beige solid. MS (apci) m/z=468.1 (M+H−H2O).

Workup

extractionextracted with DCM in a phase separator cartridge
concentrationThe combined organic extracts were concentrated

Sources & evidence

ORD record: ord-8635514d6eae4246904be332a560e143
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933084B2

Reaction notes

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