Formic Acid → HCID 14347178, compound

HRID 2352167Notes

Reaction equation

HRID 2352167 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].[CH:23]([NH2:25])=[O:24].C(O)=O>O>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([CH:1]([NH:25][CH:23]=[O:24])[CH3:2])=[CH:5][CH:6]=3)[N:16]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 713FormamideHCID 14347036HCID 14347036, compound

Product 1

HCID 14347178HCID 14347178, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.25 g of N-(4-acetylphenyl)-4-(3-pyridinyl)-2-pyrimidinamine, 100 ml of formamide and 31 ml, of 98% formic acid was refluxed with stirring overnight. The solvents were then boiled off for 1/2 hour, the reaction cooled and poured into one liter of water. This was extracted with 725 ml of chloroform. The chloroform extract was back washed with 150 ml of water, then dried, filtered and evaporated to a foam. The foam was partitioned between chloroform and water. An equal volume of saturated potassium bicarbonate was added. The organic phase was separated, dried, filtered and evaporated to a foam. This foam was chromatographed on silica gel topped with a thin layer of hydrous magnesium silicate and eluted with chloroform (first four fractions), then with 2% methanol in chloroform (last two fractions). The sixth (final) fraction was evaporated and then crystallized from chloroform-hexane, giving 1.05 g of the desired product as cream colored crystals, mp 118°-121° C.

Workup

  1. waitThe solvents were then boiled off for 1/2 hour
  2. temperaturethe reaction cooled
  3. extractionThis was extracted with 725 ml of chloroform
  4. extractionThe chloroform extract
  5. washwas back washed with 150 ml of water
  6. customdried
  7. filtrationfiltered
  8. customevaporated to a foam
  9. customThe foam was partitioned between chloroform and water
  10. additionAn equal volume of saturated potassium bicarbonate was added
  11. customThe organic phase was separated
  12. customdried
  13. filtrationfiltered
  14. customevaporated to a foam
  15. customThis foam was chromatographed on silica gel
  16. washeluted with chloroform (first four fractions), then with 2% methanol in chloroform (last two fractions)
  17. customThe sixth (final) fraction was evaporated
  18. customcrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-e62978ec86c8435eb2064a9f528e91a4
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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