Triphenylphosphine → 9-benzyloxy-6-[1-(4-bromophenyl)-cyclopentylmethyl]-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169276Notes

Reaction equation

HRID 2169276 reaction equation
O[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5]([C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]2([C:28]3[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=3)[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:14]([O:13][C:12]1[C:11](=[O:21])[N:10]=[C:9]([CH2:22][C:23]2([C:28]3[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=3)[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]2[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5](=[O:6])[C:7]=12)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 178457435HCID 178457435, compound

Product 1

HCID 867259269-benzyloxy-6-[1-(4-bromophenyl)-cyclopentylmethyl]-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-benzyloxy-2-[1-(4-bromophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (233) (0.7 g, 1.23 mmol) and triphenyl phosphine (0.807 g, 3.08 mmol) in dr y dichloromethane (10 mL) was added diethyl azidocarboxylate (0.58 mL, 3.69 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h. After completion, the solvent was evaporated and the crude product was purified by 100-200 silica gel column chromatography using 2% methanol in dichloromethane as the eluent to give 9-benzyloxy-6-[1-(4-bromophenyl)-cyclopentylmethyl]-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (234) (0.40 g, 59%) as a white solid.

Workup

  1. customAfter completion, the solvent was evaporated
  2. customthe crude product was purified by 100-200 silica gel column chromatography

Sources & evidence

ORD record
ord-5d230a4af5df4225a627bcd29a0f4e7a
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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