Benzyl chloroformate → HCID 59514555, compound

HRID 1159679Notes

Reaction equation

HRID 1159679 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[N:12]=[C:11]([N:13]([CH3:15])[CH3:14])[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9][N:8]=2)=[CH:4][CH:3]=1.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>N1C=CC=CC=1.ClCCl>[CH2:27]([O:26][C:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:12]=[C:11]([N:13]([CH3:15])[CH3:14])[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9][N:8]=2)=[CH:21][CH:22]=1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 59514489HCID 59514489, compound

Product 1

HCID 59514555HCID 59514555, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl [2-(4-aminobenzyl)-4-(dimethylamino)pyrimidin-5-yl]acetate (1.50 g, 4.99 mmol) in pyridine (1.21 mL) and dichloromethane (20 mL) was added benzyl chloroformate (1.07 mL, 7.49 mmol). After stirring for 14 hours at room temperature, the reaction mixture was concentrated under reduced pressure. The remaining residue was chromatographed on silica gel (NH silica gel, hexane/ethyl acetate 2:1) to give methyl [2-(4-{[(benzyloxy)carbonyl]amino}-benzyl)-4-(dimethylamino)pyrimidin-5-yl]acetate (1.99 g, 92%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe remaining residue was chromatographed on silica gel (NH silica gel, hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-79e8cb8ee0e94620b8bbd67e81df651d
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

Loading…