Lithium hydroxide, monohydrate → HCID 86712731, compound

HRID 1779098Notes

Reaction equation

O[Li].O.C[O:5][C:6](=[O:42])[CH2:7][C:8]1[CH:41]=[CH:40][CH:39]=[CH:38][C:9]=1[CH2:10][CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]2[CH:21]=[N:22][N:23]([CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)[CH:24]=2)[N:13]=1>O.C1COCC1>[C:34]([O:33][C:31]([N:28]1[CH2:29][CH2:30][CH:25]([N:23]2[CH:24]=[C:20]([NH:19][C:14]3[N:13]=[C:12]([CH2:11][CH2:10][C:9]4[CH:38]=[CH:39][CH:40]=[CH:41][C:8]=4[CH2:7][C:6]([OH:42])=[O:5])[C:17]([CH3:18])=[CH:16][N:15]=3)[CH:21]=[N:22]2)[CH2:26][CH2:27]1)=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 40 °C

Procedure

LiOH.H2O (0.302 g, 7.20 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate (A126) (0.077 g, 0.14 mmol) in H2O (1 mL) and THF (10 mL) and the resulting mixture was heated to 40° C. for 18 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (100 mL), washed with aqueous 2 M HCl (50 mL), water (100 mL), brine (50 mL) and dried over MgSO4. The volatiles were removed in vacuo to give the title compound A127 as a pale yellow solid (0.068 g, 91%); LCMS-A: rt 5.366 min; m/z 521 [M+H]+.

Workup

customThe volatiles were removed in vacuo
additionthe residue was diluted with EtOAc (100 mL)
washwashed with aqueous 2 M HCl (50 mL), water (100 mL), brine (50 mL)
dry with materialdried over MgSO4
customThe volatiles were removed in vacuo

Sources & evidence

ORD record: ord-d33fdf20bf494dfaaf192b0320d6423f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266864B2

Reaction notes

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