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

HRID 2169210Notes

Reaction equation

HRID 2169210 reaction equation
O[CH2:2][CH2:3][N:4]([CH:30]([CH3:32])[CH3:31])[C:5]([C:7]1[NH:8][C:9]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Br:29])=[N:10][C:11](=[O:21])[C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=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[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Br:29])[N:8]2[CH2:2][CH2:3][N:4]([CH:30]([CH3:32])[CH3:31])[C:5](=[O:6])[C:7]=12)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178457456HCID 178457456, compound

Product 1

HCID 867258609-benzyloxy-6-(2-bromobenzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 148.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Benzyloxy-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (70) (0.21 g, 420 μmol, Eq: 1.00) and Ph3P (143 mg, 546 μmol, Eq: 1.3) were stirred in dichloromethane (5 ml) at room temperature for ˜15 min. Then diisopropyl azodicarboxylate (116 mg, 112 μl, 546 μmol, Eq: 1.3) was added and the resulting mixture was stirred at room temperature overnight. The solvent was removed. The remaining material was purified by SiO2 flash chromatography (hexanes/ethyl acetate 5-50%, then dichloromethane/methanol 0-4% methanol). 300 mg of 9-benzyloxy-6-(2-bromobenzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (71) (˜40% pure, ˜60% yield) as light yellow solid were isolated and used as obtained.

Workup

  1. customThe solvent was removed
  2. customThe remaining material was purified by SiO2 flash chromatography (hexanes/ethyl acetate 5-50%

Sources & evidence

ORD record
ord-07fa7bc3da584b669212e6f9d7054c86
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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