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

HRID 2169200Notes

Reaction equation

HRID 2169200 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:26]([N:28]([CH2:32][CH2:33]O)[CH:29]([CH3:31])[CH3:30])=[O:27])=[N:11][C:12]([CH2:16][C:17]([CH3:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])=[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]([CH3:25])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:18])[N:11]2[CH2:33][CH2:32][N:28]([CH:29]([CH3:31])[CH3:30])[C:26](=[O:27])[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 178457455HCID 178457455, compound

Product 1

HCID 867258499-(benzyloxy)-2-isopropyl-6-(2-methyl-2-phenylpropyl)-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dioneYield 53.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(benzyloxy)-6-hydroxy-N-(2-hydroxyethyl)-N-isopropyl-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxamide (58) (35 mg, 75.5 μmol, Eq: 1.00) in dichloromethane (5.00 ml) was added triphenylphosphine (29.7 mg, 113 μmol, Eq: 1.5) at room temperature and the reaction mixture was stirred for 10 min. Then diisopropyl azodicarboxylate (22.9 mg, 22.0 μl, 113 μmol, Eq: 1.5) was added and the reaction mixture was stirred for 18 hrs at room temperature. The reaction mixture was concentrated on a rotary evaporator and chromatographed (silica gel, gradient, 2 to 5% methanol-dichloromethane) to obtain 9-(benzyloxy)-2-isopropyl-6-(2-methyl-2-phenylpropyl)-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (59) (18 mg, 53.5% yield).

Workup

  1. stirringthe reaction mixture was stirred for 18 hrs at room temperature
  2. concentrationThe reaction mixture was concentrated on a rotary evaporator
  3. customchromatographed (silica gel, gradient, 2 to 5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-ee871622eeeb4b46950cfe5abe5f6daf
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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