3-Chloroaniline → HCID 23282760, compound

HRID 369847Notes

Reaction equation

HRID 369847 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23]>C(O)CCC>[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH:23][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 23282763HCID 23282763, compound

Product 1

HCID 23282760HCID 23282760, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6.6 g (25.4 mmol) of 4-chloro-6-(2-methoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidine and 5.34 ml (50.8 mmol) of 3-chloro-aniline in 100 ml of n-butanol are heated at boiling for 1.5 hours. The reaction mixture is cooled, then filtered and washed with diethyl ether and hexane. Flash chromatography (SiO2 ; applied dry; hexane/ethyl acetate [2:1] ethanol/acetone [1:1]) yields the title compound; m.p. 221-222° C.; TLC-Rf =0.3 (hexane/ethyl acetate [1:1]); FAB-MS: (M+H)+ =351.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. washwashed with diethyl ether and hexane
  4. dry with materialFlash chromatography (SiO2 ; applied dry; hexane/ethyl acetate [2:1] ethanol/acetone [1:1])

Sources & evidence

ORD record
ord-d214e2477e73448fb6ae4ff12a42f15a
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

Loading…