Benzyl chloroformate → HCID 59514555, compound

HRID 2422166Notes

Reaction equation

HRID 2422166 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:6]([N:19]([CH3:21])[CH3:20])=[N:7][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[N:9][CH:10]=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>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:6]([N:19]([CH3:20])[CH3:21])=[N:7][C:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[CH:14][CH:13]=2)=[N:9][CH:10]=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-c1f77867ed024dbf8d8416337aa823c8
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

Loading…