9-benzyloxy-6-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione → 9-Benzyloxy-2-isopropyl-6-(1-naphthalen-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169265Notes

Reaction equation

HRID 2169265 reaction equation
O[CH2:2][CH2:3][N:4]([CH:38]([CH3:40])[CH3:39])[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(C3C=CC4C(=CC=CC=4)C=3)[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]=1)=[O:6].C(OC1C(=O)N=C(C[C:57]2([C:62]3[CH:67]=[C:66](Cl)[CH:65]=[CH:64][C:63]=3Cl)[CH2:61][CH2:60][CH2:59]C2)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([C:61]3[CH:60]=[CH:59][C:63]4[C:62](=[CH:67][CH:66]=[CH:65][CH:64]=4)[CH:57]=3)[CH2:27][CH2:26][CH2:25][CH2:24]2)[N:8]2[CH2:2][CH2:3][N:4]([CH:38]([CH3:40])[CH3:39])[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 867259049-benzyloxy-6-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneHCID 178457434HCID 178457434, compound

Product 1

HCID 867259179-Benzyloxy-2-isopropyl-6-(1-naphthalen-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 41.33%

Procedure

9-Benzyloxy-2-isopropyl-6-(1-naphthalen-2-yl-cyclopentylmethyl)-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (221) (90.0 mg, 41.33%) was synthesized as a white solid from 5-benzyloxy-6-hydroxy-2-(1-naphthalen-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (220) (225.0 mg, 0.417 mmol) following the procedure described for 9-benzyloxy-6-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (208).

Sources & evidence

ORD record
ord-edb77c1d2fc248baa85e15e78de507a5
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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