Formamide → HCID 19844077, compound

HRID 2232315Notes

Reaction equation

HRID 2232315 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]([C:20](=O)[CH3:21])[CH:17]=[CH:18][CH:19]=3)[N:8]=2)[CH:2]=1.[CH:23]([NH2:25])=[O:24]>C(O)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]([NH:25][CH:23]=[O:24])[CH3:21])[CH:17]=[CH:18][CH:19]=3)[N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 14347154HCID 14347154, compound

Product 1

HCID 19844077HCID 19844077, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 2.9 g of 1-[3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]ethanone, 40 ml of formamide and 13 ml of concentrated formic acid was refluxed for 15 hours, then cooled and evaporated. The residue was partitioned between unsaturated aqueous potassium bicarbonate and chloroform. The organic phase was separated, dried, filtered and evaporated. The residue was chromatographed on silica gel, eluting 125 ml fractions, fractions 1-4 with chloroform and fractions 5-7 with 2% methanol in chloroform. Fractions 5-7 were combined and evaporated, giving 1.25 g of the desired product as a yellow foam.

Workup

  1. temperaturewas refluxed for 15 hours
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was partitioned between unsaturated aqueous potassium bicarbonate and chloroform
  5. customThe organic phase was separated
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washeluting 125 ml fractions, fractions 1-4 with chloroform and fractions 5-7 with 2% methanol in chloroform
  11. customevaporated

Sources & evidence

ORD record
ord-8f904957ad2c47b78f6d9b461cbed50e
Source dataset
uspto-grants-1988_11
Patent number
US04788195

Reaction notes

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