Chloroacetic Acid → HCID 12904736, compound

HRID 1679901Notes

Reaction equation

HRID 1679901 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.[Cl:21][CH2:22][C:23](O)=[O:24].C(N1C=CN=C1)(N1C=CN=C1)=O>ClCCCl>[Cl:21][CH2:22][C:23]([NH:20][C:19]1[C:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])=[CH:10][C:11]2[CH:16]=[N:15][C:14]([CH3:17])=[N:13][C:12]=2[N:18]=1)=[O:24]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 12904727HCID 12904727, compound

Product 1

HCID 12904736HCID 12904736, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 3.0 g of 6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine and 50 ml of 1,2-dichloroethane is boiled on a steam bath until the distilling vapors reach a temperature of 83° C. The suspension is cooled to room temperature and 1.6 g of chloroacetic acid and 2.6 g of carbonyldiimidazole are added sequentially. The mixture is stirred at room temperature for 3 hours and the resulting solution is immediately chromatographed over 150 g of silica gel. The crude product is eluted with a 99/1 chloroform/methanol mixture. Trituration of this with ether gives pure 2-chloro-N-[6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]-pyrimidin-7-yl]acetamide, decomposing above ca 170° C.

Workup

  1. customis boiled on a steam bath until the distilling vapors
  2. customa temperature of 83° C
  3. customthe resulting solution is immediately chromatographed over 150 g of silica gel
  4. washThe crude product is eluted with a 99/1 chloroform/methanol mixture

Sources & evidence

ORD record
ord-99e07c292fd446439dcd4be3ec25d0d1
Source dataset
uspto-grants-1981_06
Patent number
US04271164

Reaction notes

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