Lithium Hydroxide → HCID 66727676, compound

HRID 2409191Notes

Reaction equation

HRID 2409191 reaction equation
[NH2:1][C:2]1[N:3]([CH3:32])[C:4](=[O:31])[C:5]([CH3:30])([CH3:29])[C@:6]([C:9]2[CH:10]=[C:11]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][C:18]=3[O:27][CH3:28])[CH:12]=[CH:13][C:14]=2[F:15])([CH3:8])[N:7]=1.[Li+].[OH-]>C1COCC1.CO.O>[NH2:1][C:2]1[N:3]([CH3:32])[C:4](=[O:31])[C:5]([CH3:29])([CH3:30])[C@:6]([C:9]2[CH:10]=[C:11]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=3[O:27][CH3:28])[CH:12]=[CH:13][C:14]=2[F:15])([CH3:8])[N:7]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 66727669HCID 66727669, compound

Product 1

HCID 66727676HCID 66727676, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 4-(3-(2-amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydropyrimidin-4-yl)-4-fluorophenylamino)-3-methoxybenzoate (example 123, 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, the residue was dissolved in aqueous HCl (0.5N) until pH=5 and extracted with dichloromethane. The organic phase was separated, dried over Na2SO4 and evaporated to yield a white solid. The solid material was triturated with Et2O, filtered and dried to yield the title compound as a white solid. MS (ESI): m/z=429.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in aqueous HCl (0.5N) until pH=5
  3. extractionextracted with dichloromethane
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto yield a white solid
  8. customThe solid material was triturated with Et2O
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-f310d0f4ccf8436da2a501291a7883ac
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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