2-Furancarboxylic acid → HCID 12904763, compound

HRID 1679900Notes

Reaction equation

HRID 1679900 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:19]([NH2:20])=[N:18][C:12]2[N:13]=[C:14]([CH3:17])[N:15]=[CH:16][C:11]=2[CH:10]=1.[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](O)=[O:27].C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)(Cl)Cl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:19]([NH:20][C:26]([C:22]2[O:21][CH:25]=[CH:24][CH:23]=2)=[O:27])=[N:18][C:12]2[N:13]=[C:14]([CH3:17])[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 69192-Furancarboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 12904727HCID 12904727, compound

Product 1

HCID 12904763HCID 12904763, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 3.0 g of 6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine and 1.8 g of 2-furoic acid in 50 ml of chloroform is boiled on a steam bath until the distilling vapors reach a temperature of 61° C. The mixture is cooled to about 40° C. and 2.6 g of carbonyldiimidazole is added cautiously. Gas is evolved. When gas evolution has ceased, the resulting solution is heated at reflux for 30 hours. The cooled reaction mixture is chromatographed directly on a column of 150 g of silica gel. The crude product is eluted with a 99/1 chloroform/methanol mixture. This is purified by trituration with ether and recrystallization of the resulting solid from a chloroform/ether mixture. N-[6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-yl]-2-furancarboxamide is obtained as yellow crystals, mp 228°-230.5° C.

Workup

  1. customis boiled on a steam bath until the distilling vapors
  2. customa temperature of 61° C
  3. temperaturethe resulting solution is heated
  4. temperatureat reflux for 30 hours
  5. customThe cooled reaction mixture
  6. customis chromatographed directly on a column of 150 g of silica gel
  7. washThe crude product is eluted with a 99/1 chloroform/methanol mixture
  8. customThis is purified by trituration with ether and recrystallization of the resulting solid from a chloroform/ether mixture

Sources & evidence

ORD record
ord-8daa19c9213041929fd477ba14723832
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

Loading…