Hydrochloric Acid → Tert-butyl 4-(5-(1-(4-fluorophenyl)-2-hydroxyethyl)pyrimidin-2-yl)piperazine-1-carboxylat

HRID 1498858Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[N:14][CH:15]=2)=[CH2:9])=[CH:4][CH:3]=1.B.C1C[O:33]CC1.[OH-].[Na+].OO.Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[N:12][C:13]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[N:14][CH:15]=2)[CH2:9][OH:33])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Tert-butyl 4-(5-(1-(4-fluorophenyl)vinyl)pyrimidin-2-yl)piperazine-1-carboxylate (1.2 g, 3.12 mmol) was dissolved in THF (30 mL) and then cooled to 0° C., followed by the addition of BH3.THF (6.24 mL, 6.24 mmol) dropwise. The mixture was stirred at RT for 3 h. To the mixture was added H2O in THF (10%, 8 mL), a solution of NaOH (1.25 g) in 30 mL H2O and H2O2 (35%, 18 g) sequentially at 0° C. The mixture was stirred at RT overnight. The mixture was acidified with 1 N HCl and extracted with EA (3×50 mL). The organic phases were washed with aqueous NaHCO3 (50 mL), brine (50 mL), dried over sodium sulfate, filtered, concentrated and purified by silica gel chromatography (DCM:CH3OH=30:1) to get the title compound as a white solid (0.3 g, 24%). MS (ES+) C21H27FN4O3 requires: 402. found: 403 [M+H]+.

Workup

customsequentially at 0° C
stirringThe mixture was stirred at RT overnight
extractionextracted with EA (3×50 mL)
washThe organic phases were washed with aqueous NaHCO3 (50 mL), brine (50 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography (DCM:CH3OH=30:1)

Sources & evidence

ORD record: ord-072af6fa82ac44cc92791c95139ed7d7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09200002B2

Reaction notes

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