Sodium hydride → HCID 23562818, compound

HRID 1058855Notes

Reaction equation

HRID 1058855 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[H-].[Na+].Cl[C:25]1[N:30]=[CH:29][CH:28]=[CH:27][N:26]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:25]2[N:30]=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 7019130Boc-Tyr-OMe

Product 1

HCID 23562818HCID 23562818, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of N-BOC-L-tyrosine methyl ester (3.0 g, 10.2 mmol) in DMF (5 ml) was added to a suspension of NaH (60% in oil, 11.2 mmol, 447 mg) in DMF (10 ml). After 10 min, a solution of 2-chloropyrimidine (11.2 mmol, 1.28 g) in DMF (3 ml) was added and the mixture stirred overnight. The reaction was quenched with water, diluted EtOAc and washed with water and brine. The EtOAc layer was dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography [SiO2, EtOAc/hexane, 1:1] gave the title compound. δH (DMSO d6) 8.62 (2H, d, J 4.8 Hz), 7.37 (1H, d, J 8.1 Hz), 7.28 (2H, d, J 8.4 Hz), 7.24 (1H, t, J 4.8 Hz), 7.09 (2H, d, J 8.4 Hz), 4.18 (1H, m), 3.01 (1H, dd, J 13.8, 4.6 Hz), 1.33 (9H, s).

Workup

  1. customThe reaction was quenched with water, diluted EtOAc
  2. washwashed with water and brine
  3. dry with materialThe EtOAc layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography [SiO2, EtOAc/hexane, 1:1]

Sources & evidence

ORD record
ord-cd24335fd862423bb1246f43d9a9d440
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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