Diethyl Oxalate → HCID 135670768, compound

HRID 728017Notes

Reaction equation

HRID 728017 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[N:8]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH2:23][CH3:24])[NH:10][C:11](=[O:14])[C:12]=1[NH2:13].C(N(CC)CC)C.[C:32](OCC)(=[O:38])[C:33](OCC)=[O:34]>COC(O)C>[CH2:22]([O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:9]1[NH:10][C:11](=[O:14])[C:12]2[NH:13][C:33](=[O:34])[C:32](=[O:38])[NH:6][C:7]=2[N:8]=1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 8471TriethylamineHCID 1363645694,5-Diamino-2-(propoxyphenyl)pyrimidin-6-one sulphate

Product 1

HCID 135670768HCID 135670768, compound

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

A stirred mixture of 4,5-diamino-2-(2-propoxyphenyl)pyrimidin-6-one sulphate (1.0 g), triethylamine (0.42 ml) and diethyl oxalate (1.2 ml) in methoxyethanol (10 ml) was heated under reflux for 7 hours. The reaction mixture was stirred overnight at ambient temperature and a precipitate was collected and washed with water and ethanol to afford a crude product (0.70 g, m.p. 312°-315° C.). The crude product together with another sample (0.34 g) similarly prepared was twice recrystallised from dimethylformamide to afford the title compound, 0.40 g, m.p. 320°-321° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. customa precipitate was collected
  4. washwashed with water and ethanol
  5. customto afford a crude product (0.70 g, m.p. 312°-315° C.)
  6. customwas twice recrystallised from dimethylformamide

Sources & evidence

ORD record
ord-259072c023a24206ad006310a65f88cc
Source dataset
uspto-grants-1991_09
Patent number
US05047404

Reaction notes

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