Ethanol → HCID 59239148, compound

HRID 1697895Notes

Reaction equation

HRID 1697895 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:13][C:12]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)=[N:11][C:10]=2[C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>O.CO.ClCCl>[CH2:1]([N:8]1[CH2:16][C:15]2[C:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[N:13][C:12]([C:23]3[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=3)=[N:11][C:10]=2[C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 59239359HCID 59239359, compound

Product 1

HCID 59239148HCID 59239148, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

6-benzyl-4-morpholino-2-(4-nitrophenyl)-5H-pyrrolo[3,4-d]pyrimidin-7(6H)-one (cy) (0.112 g, 0.260 mmol), stannous chloride dihydrate (0.310 g, 1.36 mmol) and ethanol (2.00 mL) were combined and stirred at 80° C. for 1 hour. The mixture was diluted with H2O and 10% MeOH in dichloromethane, extracted 3 times with 10% MeOH in dichloromethane. The combined organic extract was dried over Magnesium sulfate and concentrated to give compound cz (0.083 g, 80%): LC-MS: m/z=+434 (M+H)+; 1H NMR (400 MHz, DMSO) δ 9.10 (s, 2H), 7.24 (d, J=8.6, 2H), 7.14 (s, 2H), 6.91 (d, J=8.6, 2H), 4.64 (d, J=27.1, 4H), 3.80-3.60 (m, 11H).

Workup

  1. extractionextracted 3 times with 10% MeOH in dichloromethane
  2. extractionThe combined organic extract
  3. dry with materialwas dried over Magnesium sulfate
  4. concentrationconcentrated
  5. customto give compound cz (0.083 g, 80%)

Sources & evidence

ORD record
ord-e4cfde2a52f74a5baed3cf030a3fe541
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

Loading…