9-Benzyloxy-6-(2'-chloro-biphenyl-2-ylmethyl)-8-hydroxy-2-isopropyl-3,4-dihydro-2H,8H-pyrazino[1,2-c]pyrimidin-1-one → 6-(2'-Chloro-biphenyl-2-ylmethyl)-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169147Notes

Reaction equation

HRID 2169147 reaction equation
C([O:8][C:9]1[CH:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[N:11]2[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[C:33](=[O:34])[C:10]=12)C1C=CC=CC=1.C1(C2C=CC=CC=2)C=CC=CC=1CC1N2CCN(C)C(=O)C2=C(O)C(=O)N=1>>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][C:12]1[N:11]2[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[C:33](=[O:34])[C:10]2=[C:9]([OH:8])[C:14](=[O:15])[N:13]=1

Participants

3

Reactant 2

HCID 867258009-Benzyloxy-6-(2'-chloro-biphenyl-2-ylmethyl)-8-hydroxy-2-isopropyl-3,4-dihydro-2H,8H-pyrazino[1,2-c]pyrimidin-1-oneHCID 867258016-biphenyl-2-ylmethyl-9-hydroxy-2-methyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

Product 1

HCID 867258046-(2'-Chloro-biphenyl-2-ylmethyl)-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dioneYield 37.07%

Procedure

6-(2′-Chloro-biphenyl-2-ylmethyl)-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (12-04) (107 mg, 37.07%) was synthesized as an off-white solid from 9-benzyloxy-6-(2′-chloro-biphenyl-2-ylmethyl)-8-hydroxy-2-isopropyl-3,4-dihydro-2H,8H-pyrazino[1,2-c]pyrimidin-1-one (11-04) (350 mg, 0.682 mmol) following the procedure as described for 6-biphenyl-2-ylmethyl-9-hydroxy-2-methyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (12-01).

Sources & evidence

ORD record
ord-d8e59a71ea98471db4dbf9ce13ea88c1
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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