Oxalic Acid → HCID 86659302, compound

HRID 2283454Notes

Reaction equation

HRID 2283454 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]1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 11528435753015-44-0

Product 1

HCID 86659302HCID 86659302, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%).

Workup

  1. customThe salt precipitated
  2. temperatureupon further warming of the solution
  3. additionthe mixture was diluted with ethanol (6 mL)
  4. waitwas left
  5. filtrationThe light-beige powder was filtered
  6. washwashed with ethanol
  7. customdried in a vacuum oven at 50° C. for 6 h
  8. customto give 1.40 g (92.3%) of a creamy-white, fluffy powder, mp 149-151° C

Sources & evidence

ORD record
ord-6af8e33238774e4a88287ab7aa4c7116
Source dataset
uspto-grants-2015_09
Patent number
US09145396B2

Reaction notes

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