Lithium Hydroxide → HCID 66727679, compound

HRID 2409190Notes

Reaction equation

HRID 2409190 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([C@:20]3([CH3:31])[C:25]([CH3:27])([CH3:26])[C:24](=[O:28])[N:23]([CH3:29])[C:22]([NH2:30])=[N:21]3)[CH:14]=2)[CH:5]=1.[Li+].[OH-]>C1COCC1.CO.O>[NH2:30][C:22]1[N:23]([CH3:29])[C:24](=[O:28])[C:25]([CH3:26])([CH3:27])[C@:20]([C:15]2[CH:14]=[C:13]([NH:12][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=3[O:10][CH3:11])[C:3]([OH:32])=[O:2])[CH:18]=[CH:17][C:16]=2[F:19])([CH3:31])[N:21]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 66727658HCID 66727658, compound

Product 1

HCID 66727679HCID 66727679, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl-3-(3-(2-amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenylamino)-4-methoxybenzoate (example 122, 0.05 mmol) in THF (1 ml), MeOH (0.3 ml) and H2O (0.3 ml) was added LiOH (1N, 0.1 mmole) and the reaction mixture was stirred at room temperature for 12 h. The mixture was concentrated in vacuo and the residue diluted with aqueous HCl (0.5N) until pH=5 and extracted with dichloromethane. The organic phase was dried, evaporated and the residue triturated with Et2O to give the title compound as a white solid. MS (ESI): m/z=429.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue diluted with aqueous HCl (0.5N) until pH=5
  3. extractionextracted with dichloromethane
  4. customThe organic phase was dried
  5. customevaporated
  6. customthe residue triturated with Et2O

Sources & evidence

ORD record
ord-d8f2ed3bbae2419ba547f44e0a59919f
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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