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

HRID 2169363Notes

Reaction equation

HRID 2169363 reaction equation
[CH:1]1([N:4]([CH2:35][CH2:36]O)[C:5]([C:7]2[C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]3([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=4)[CH2:27][CH2:26][CH2:25][CH2:24]3)[N:8]=2)=[O:6])[CH2:3][CH2:2]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>[CH2:14]([O:13][C:12]1[C:11](=[O:21])[N:10]=[C:9]([CH2:22][C:23]2([C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]2[CH2:36][CH2:35][N:4]([CH:1]3[CH2:2][CH2:3]3)[C:5](=[O:6])[C:7]=12)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178519969HCID 178519969, compound

Product 1

HCID 867259949-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-cyclopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 151.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid cyclopropyl-(2-hydroxyethyl)-amide (326) (90 mg, 0.17 mmol) and triphenylphosphine (90.5 mg, 0.35 mmol) were taken up in dichloromethane (3 ml) at room temperature followed by the slow addition of diisopropyl azodicarboxylate (52.34 mg, 0.26 mmol) and stirring for 1 h. Dichloromethane (15 ml) was added to the reaction mixture, which was subsequently washed with water (10 ml) and brine (10 ml). The organic part was dried and concentrated under reduced pressure. The obtained residue was purified by normal silica column using 30% ethyl acetate in hexane to get 9-benzyloxy-6-[1-(4-chlorophenyl)-cyclopentylmethyl]-2-cyclopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (327) (130 mg, 56%; 2 steps) as a sticky yellow solid.

Workup

  1. washwas subsequently washed with water (10 ml) and brine (10 ml)
  2. customThe organic part was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by normal silica column

Sources & evidence

ORD record
ord-92f87f250dad4fa2a5878afc5ac2d83c
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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