Lithium hydroxide, monohydrate → HCID 86712644, compound

HRID 1778975Notes

Reaction equation

O[Li].O.C[O:5][C:6](=[O:43])[CH2:7][C:8]1[CH:42]=[CH:41][CH:40]=[CH:39][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]=[CH:22][C:23]([CH:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)=[N:24][CH:25]=2)[N:13]=1>O.C1COCC1>[C:35]([O:34][C:32]([N:29]1[CH2:28][CH2:27][CH:26]([C:23]2[N:24]=[CH:25][C:20]([NH:19][C:14]3[N:13]=[C:12]([CH2:11][CH2:10][C:9]4[CH:39]=[CH:40][CH:41]=[CH:42][C:8]=4[CH2:7][C:6]([OH:43])=[O:5])[C:17]([CH3:18])=[CH:16][N:15]=3)=[CH:21][CH:22]=2)[CH2:31][CH2:30]1)=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

Conditions

Temperature: 40 °C

Procedure

LiOH.H2O (442 mg, 10.5 mmol) was added to a stirred solution of tert-butyl 4-(5-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate (A18) (115 mg, 0.211 mmol) in water (4 mL) and THF (40 mL) and the resulting mixture heated at 40° C. for 18 hours. On cooling the volatiles were removed in vacuo and the residue taken up in EtOAc (100 mL). The resulting solution was washed with water (100 mL), brine (50 mL) and dried over MgSO4. The volatiles were removed in vacuo to give the title compound A19 as a clear oil (96 mg, 86%); LCMS-A: rt 5.137 min; m/z 532 [M+H]+.

Workup

temperatureOn cooling the volatiles
customwere removed in vacuo
washThe resulting solution was washed with water (100 mL), brine (50 mL)
dry with materialdried over MgSO4
customThe volatiles were removed in vacuo

Sources & evidence

ORD record: ord-2bb1e90a7df6484ebb6a9bcd1d23594a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266864B2

Reaction notes

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