Hydrochloric Acid → 6-((1-(4-chlorophenyl)cyclopentyl)methyl)-9-hydroxy-2-phenyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione

HRID 2169192Notes

Reaction equation

C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:29][CH2:30][N:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:32](=[O:33])[C:10]=12)C1C=CC=CC=1.Cl.C([O-])(O)=O.[Na+]>CO>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:17]2([CH2:16][C:12]3[N:11]4[CH2:29][CH2:30][N:31]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[C:32](=[O:33])[C:10]4=[C:9]([OH:8])[C:14](=[O:15])[N:13]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 9-(benzyloxy)-6-((1-(4-chlorophenyl)cyclopentyl)methyl)-2-phenyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (49) (88.5 mg, 164 μmol, Eq: 1.00) in methanol (5 ml) was added HCl (conc) (240 mg, 0.2 ml, 6.58 mmol, Eq: 40.2). The reaction mixture was heated at 70° C. for 18 hrs, neutralized with saturated aqueous NaHCO3 solution, extracted with dichloromethane, dried (MgSO4), concentrated, triturated with diethyl ether, filtered, and dried to obtain 6-((1-(4-chlorophenyl)cyclopentyl)methyl)-9-hydroxy-2-phenyl-3,4-dihydro-1H-pyrazino[1,2-c]pyrimidine-1,8(2H)-dione (50) (pink powder, 48.2 mg, 107 μmol, 65.4% yield).

Workup

extractionextracted with dichloromethane
dry with materialdried (MgSO4)
concentrationconcentrated
customtriturated with diethyl ether
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-2bf8d7fbceca4a5e9e5b7aa08b25be94
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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