3-Chloroaniline → 4-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369830Notes

Reaction equation

HRID 369830 reaction equation
CN1C(=O)N(C)CCC1.Cl[C:11]1[C:12]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[NH:17][C:13]=2[N:14]=[CH:15][N:16]=1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30].C(O)C.C1COCC1>C(O)CCC>[Cl:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH:30][C:11]1[C:12]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[NH:17][C:13]=2[N:14]=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 79323-ChloroanilineHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 21873804Tetrahydrofuran ethanolHCID 232826944-chloro-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 99490364-(3-Chloro-anilino)-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

Under an argon atmosphere, 40 ml of DMPU are added to 6.53 g (28.3 mmol) of 4-chloro-6-(pyrid-2-yl)-7H-pyrrolo[2,3-d]pyrimidine and 4.46 ml (42.5 mmol) of 3-chloro-aniline in 90 ml of n-butanol and the reaction mixture is stirred at 140° C. for 12 hours. The dark-brown suspension is cooled and filtered. Further product can be obtained from the mother liquor by precipitation with 100 ml of water. Digestion with ethanol/THF yields the title compound; m.p.>300° C.; 1H-NMR (360 MHz, DMSO-d6): 12.49 and 9.66 (2s, 2H), 8.63 (d, J=5, 1H), 8.40 and 8.25 (2s, 2H), 7.91 (m, 2H), 7.84 (d, J=8, 1H), 7.57 (s, 1H), 7.33 (m, 2H), 7.06 (d, J=8, 1H); HPLC: tRet (Grad20)=10.1 min; MS: (M)+ =321.

Workup

  1. temperatureThe dark-brown suspension is cooled
  2. filtrationfiltered
  3. customFurther product can be obtained from the mother liquor by precipitation with 100 ml of water

Sources & evidence

ORD record
ord-0749ec6cb92e42b6a906449d05c66d75
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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