Lithium Chloride → 2-(2-Hydroxy-3-phenyl-propylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 33978Notes

Reaction equation

HRID 33978 reaction equation
[C:1]1([CH2:7][C:8](=[O:35])[CH2:9][NH:10][C:11]2[N:16]([CH3:17])[C:15](=[O:18])[C:14]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[C:13]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.[Cl-].[Li+].CC1(C)[C@@]23C4(ON4S(=O)(=O)C2)C[C@@H]1CC3>C1COCC1>[C:1]1([CH2:7][CH:8]([OH:35])[CH2:9][NH:10][C:11]2[N:16]([CH3:17])[C:15](=[O:18])[C:14]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[C:13]([C:29]3[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 433294Lithium ChlorideHCID 2724682Lithium diisopropylamideHCID 115109142-[3-Phenyl-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-oneHCID 16212266HCID 16212266, compound

Product 1

HCID 116626342-(2-Hydroxy-3-phenyl-propylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-phenyl-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (123 mg, 0.27 mmol) in THF (5 mL) at −78° C. was added LDA (Aldrich, 2.0 M in THF, 0.4 mL). The mixture was stirred for 1 h. Lithium chloride (30 mg) was added. After 5 minutes, (1S)-(+)-(10-camphorsulfonyl)oxaziridine (200 mg, 0.87 mmol) was added. The mixture was stirred at −78 for 2 hours, and quenched with water (5 mL) and ethyl acetate (80 mL). The solution was washed with brine (3×50 mL), dried, and evaporated. The crude product was purified by preparative TLC (6% MeOH/CH2Cl2). 8 mg (7%) solids. M+1=477.2.

Workup

  1. waitAfter 5 minutes
  2. stirringThe mixture was stirred at −78 for 2 hours
  3. customquenched with water (5 mL) and ethyl acetate (80 mL)
  4. washThe solution was washed with brine (3×50 mL)
  5. customdried
  6. customevaporated
  7. customThe crude product was purified by preparative TLC (6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b2660609329440c5876c5bf50dd10d4b
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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