Triphenylphosphine → 9-(benzyloxy)-6-((1-(4-chlorophenyl)cyclopentyl)methyl)-2-phenyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione

HRID 2169191Notes

Reaction equation

HRID 2169191 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:29]([N:31]([CH2:38][CH2:39]O)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:30])=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:39][CH2:38][N:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:29](=[O:30])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178519970HCID 178519970, compound

Product 1

HCID 867258419-(benzyloxy)-6-((1-(4-chlorophenyl)cyclopentyl)methyl)-2-phenyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dioneYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(benzyloxy)-2-((1-(4-chlorophenyl)cyclopentyl)methyl)-6-hydroxy-N-(2-hydroxyethyl)-N-phenylpyrimidine-4-carboxamide (48) (100.1 mg, 179 μmol, Eq: 1.00) in dichloromethane (5 ml) at room temperature was added triphenylphosphine (70.6 mg, 269 μmol, Eq: 1.5) and stirred for 10 min. Then diisopropyl azodicarboxylate (54.4 mg, 52.3 μl, 269 μmol, Eq: 1.5) was added and the reaction mixture was stirred for 18 hrs, concentrated, and chromatographed (silica gel, gradient 0 to 5% methanol-dichloromethane) to obtain 9-(benzyloxy)-6-((1-(4-chlorophenyl)cyclopentyl)methyl)-2-phenyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (49) (white foam, 88.5 mg, 164 μmol, 91.4% yield).

Workup

  1. stirringthe reaction mixture was stirred for 18 hrs
  2. concentrationconcentrated
  3. customchromatographed (silica gel, gradient 0 to 5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-3bc229b119d84f49a396bd8e3b9ce637
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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