Lithium hydroxide, monohydrate → HCID 86712708, compound

HRID 1779065Notes

Reaction equation

HRID 1779065 reaction equation
O[Li].O.[CH3:4][O:5][C:6]1[C:7]([CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH2:40][C:41]([O:43]C)=[O:42])=[N:8][C:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[N:10][CH:11]=1>C1COCC1.O.CO>[C:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][CH:19]([C:16]2[CH:15]=[CH:14][C:13]([NH:12][C:9]3[N:8]=[C:7]([CH2:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[CH2:40][C:41]([OH:43])=[O:42])[C:6]([O:5][CH3:4])=[CH:11][N:10]=3)=[CH:18][CH:17]=2)[CH2:20][CH2:21]1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712707HCID 86712707, compound

Product 1

HCID 86712708HCID 86712708, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (0.025 g, 0.59 mmol) was added to a solution of tert-butyl 4-(4-((5-methoxy-4-(2-(2-methoxy-2-oxoethyl)phenethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A100) (0.11 g, 0.20 mmol) in THF (7 mL), water (1.5 mL) and MeOH (1 mL) and the resulting mixture stirred at room temperature for 17 hours. The volatiles were removed in vacuo and the residue was partitioned between 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 combined organic layers were washed with brine (50 mL), dried over MgSO4 and the volatiles removed in vacuo to give the title compound A101 as a pale yellow oil (0.099 g, 92%); 1H NMR (400 MHz, d4-MeOH) δ 7.98 (s, 1H), 7.52 (d, J=8.5 Hz, 2H), 7.22-7.04 (m, 6H), 4.16 (d, J=13.1 Hz, 2H), 3.76 (s, 3H), 3.71 (s, 2H), 2.96-2.88 (m, 4H), 2.88-2.70 (m, 2H), 2.65-2.55 (m, 1H), 1.76 (d, J=12.3 Hz, 2H), 1.59-1.49 (m, 2H), 1.46 (s, 9H). LCMS-A: rt 6.35 min; m/z 547.3 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between 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. washThe combined organic layers were washed with brine (50 mL)
  6. dry with materialdried over MgSO4
  7. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-f9788dea116742bbae71f879416d2315
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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