9-benzyloxy-6-(2,3-dichlorobenzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione → 9-Benzyloxy-6-(2-cyclohex-1-enyl-benzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169228Notes

Reaction equation

HRID 2169228 reaction equation
O[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5]([C:7]1[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([OH:21])[N:10]=[C:9]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=2)[N:8]=1)=[O:6].C(OC1C(=O)N=C(CC2C=CC=C(Cl)C=2Cl)N2CCN(C(C)C)C(=O)C=12)C1C=CC=CC=1>>[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[C:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]=2)[N:8]2[CH2:2][CH2:3][N:4]([CH:35]([CH3:37])[CH3:36])[C:5](=[O:6])[C:7]=12)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 867258689-benzyloxy-6-(2,3-dichlorobenzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneHCID 178457450HCID 178457450, compound

Product 1

HCID 867258769-Benzyloxy-6-(2-cyclohex-1-enyl-benzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 44.2%

Procedure

9-Benzyloxy-6-(2-cyclohex-1-enyl-benzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (156) (42.5 mg, 44.15%) as an off-white solid was synthesized from 5-benzyloxy-2-(2-cyclohex-1-enyl-benzyl)-6-hydroxypyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (155) (100 mg, 0.199 mmol) following the procedure as described for 9-benzyloxy-6-(2,3-dichlorobenzyl)-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (134).

Sources & evidence

ORD record
ord-639efe4dae2b440fac7907c3db369d65
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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