Lithium hydroxide, monohydrate → HCID 86712636, compound

HRID 1778964Notes

Reaction equation

HRID 1778964 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:25]=[CH:24][C:23]([N: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)=[CH:22][CH:21]=2)[N:13]=1>C1COCC1.O.CO>[C:35]([O:34][C:32]([N:29]1[CH2:28][CH2:27][N:26]([C:23]2[CH:22]=[CH:21][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:25][CH:24]=2)[CH2:31][CH2:30]1)=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712635HCID 86712635, compound

Product 1

HCID 86712636HCID 86712636, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (24 mg, 0.56 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate (A8) (44 mg, 0.081 mmol) in THF (7 mL), water (1.5 mL) and MeOH (1 mL) and the resulting mixture was stirred at room temperature for 24 hours. The volatiles were removed in vacuo and the resulting residue was diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organic layers were combined, washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound A9 as brown oily residue (36 mg, 84%); LCMS-A: rt 5.737 min; m/z 532.2 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe resulting residue was diluted with EtOAc (50 mL) and saturated aqueous NaHCO3 (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49fcb650a0f84c91a80a9d5e26dc28a7
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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