3-Chloroaniline → HCID 10808671, compound

HRID 2293120Notes

Reaction equation

HRID 2293120 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24]>C(O)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH:24][C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([CH3:12])[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 14754767-benzyl-4-chloro-5,6-dimethylpyrrolo[2,3-d]pyrimidine

Product 1

HCID 10808671HCID 10808671, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.6 g of 4-chloro-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]pyrimidine and 0.28 ml of m-chloroaniline are heated at reflux in 10 ml of ethanol for 17 hours. The brown solution is concentrated to dryness by evaporation, the residue is taken up in ethyl acetate, and the ethyl acetate solution is washed until neutral with sodium hydrogen carbonate solution and water, dried and concentrated by evaporation. The residue is crystallised from ethyl acetate/hexane. 4-(m-Chloroanilino)-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]pyrimidine is obtained in the form of white crystals having a melting point of 132°-133° C.

Workup

  1. concentrationThe brown solution is concentrated to dryness by evaporation
  2. washthe ethyl acetate solution is washed until neutral with sodium hydrogen carbonate solution and water
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customThe residue is crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-7ac61f5da6e44320903aff19d2477106
Source dataset
uspto-grants-1997_11
Patent number
US05686457

Reaction notes

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