Oxalic Acid → HCID 86659302, compound
Reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[NH:7]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[C:14]2[CH:15]=[N:16][CH:17]=[N:18][CH:19]=2)[CH2:8]1>C(O)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[NH:7]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[N:18][CH:17]=[N:16][CH:15]=2)[CH2:8]1Participants
4
Reagents, catalysts & solvents 1
Procedure
Oxalic acid (0.516 g, 5.73 mmol) was added as a solid to a stirring, warm solution of (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine (1.00 g, 5.70 mmol) in ethanol (10 mL). The salt precipitated upon further warming of the solution. To facilitate stirring, the mixture was diluted with ethanol (6 mL), and the lumps were broken with a spatula. The mixture was cooled to ambient temperature and was left standing overnight. The light-beige powder was filtered, washed with ethanol, and dried in a vacuum oven at 50° C. for 6 h to give 1.40 g (92.3%) of a creamy-white, fluffy powder, mp 149-151° C. 1H NMR (DMSO-d6): δ 9.03 (s, 1H), 8.86 (s, 2H), 6.56 (m, 2H), 3.40 (dd, 1H), 3.31 (m, 1H), 3.18 (m, 1H), 3.08 (m, 1H), 2.96 (dd, 1H), 2.15 (m, 1H), 1.80 (m, 1H), 13C NMR (DMSO-d6): δ 164.90 (C═O of oxalic acid), 156.97, 154.17, 133.66, 130.31, 124.20, 48.70, 44.33, 40.98, 30.42. Elemental analysis: Calculated for C10H13N3.C2H2O4 (C, 54.33%; H, 5.70%, N, 15.84%). Found (C, 54.39%, 54.29%; H, 5.68%, 5.66%; N, 15.68%, 15.66%).