3-Chloroaniline → HCID 23282748, compound

HRID 369858Notes

Reaction equation

HRID 369858 reaction equation
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[NH:8][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)CCC>[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]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 23282786HCID 23282786, compound

Product 1

HCID 23282748HCID 23282748, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4 g of 4-chloro-5-methyl-6-(4-methoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidine and 8.45 ml of 3-chloro-aniline are heated under reflux in 400 ml of n-butanol for 20 hours. The brown solution is concentrated, the desired product already precipitating. The solution is stored overnight in a refrigerator and the product is filtered off with suction and washed with hexane/ethyl acetate, yielding the title compound in the form of colourless crystals; m.p. 265-268° C.; FAB-MS: (M+H)+ =365.

Workup

  1. concentrationThe brown solution is concentrated
  2. customthe desired product already precipitating
  3. filtrationthe product is filtered off with suction
  4. washwashed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-599cb68bb4664a0199e4553d94faa142
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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