Formamide → HCID 19844077, compound

HRID 2352185Notes

Reaction equation

HRID 2352185 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 chormatographed 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. washeluting 125 ml fractions, fractions 1-4 with chloroform and fractions 5-7 with 2% methanol in chloroform
  10. customevaporated

Sources & evidence

ORD record
ord-eb79f5ecb2d7493188dccdb8cb1c951b
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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