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

HRID 2169179Notes

Reaction equation

HRID 2169179 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:29]([N:31]([CH2:40][CH2:41]O)[CH:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:33])=[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:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:41][CH2:40][N:31]([CH:32]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH3:33])[C:29](=[O:30])[C:10]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178436098HCID 178436098, compound

Product 1

HCID 867258319-(benzyloxy)-6-((1-(4-chlorophenyl)cyclopentyl)methyl)-2-(1-phenylethyl)-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dioneYield 78.4%

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-(1-phenylethyl)pyrimidine-4-carboxamide (36) (158 mg, 270 μmol, Eq: 1.00) in dichloromethane (15 ml) at room temperature was added triphenylphosphine (106 mg, 404 μmol, Eq: 1.5). The reaction mixture was stirred for 10 min. Then diisopropyl azodicarboxylate (81.8 mg, 78.6 μl, 404 μmol, Eq: 1.5) was added. 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-(1-phenylethyl)-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (37) (colorless of 1,120 mg, 211 μmol, 78.4% 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-38c200ebbffc4cea82d1317696f7cfc1
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

Loading…