3-Chloroaniline → 4-(3-chloroanilino)-6-ethoxy-carbonyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 567749Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

Under a argon atmosphere, 29.0 g (128 mmol) of 4-chloro-6-ethoxy-carbonyl-7H-pyrrolo[2,3-d]pyrimidine and 18.0 ml (171 mmol) of 3-chloroaniline in 430 ml of n-butanol are stirred at 100° C. for 3 h (almost dissolved after≈1 h, then a thick suspension is formed). 400 ml of isopropanol/hexane (1:1) are then added to the reaction mixture cooled to≈50° C., and the product is filtered off and washed with isopropanol and hexane. Stirring in diethyl ether yields 4-(3-chloroanilino)-6-ethoxy-carbonyl-7H-pyrrolo[2,3-d]pyrimidine; 1H-NMR (DMSO-d6) 13.0 and 10.53 (2 sb, 2HN), 8.48 (s, 1H), 8.13 (m, 1H), 7.78 (dm, J=8, 1H), 7.76 (s, 1H), 7.45 (t, J=8, 1H), 7.21 (dm, J=8), 1H), 4.37 (q, J=7, 2H), 1.37 (t, J=7, 3H).

Workup

dissolutionalmost dissolved after≈1 h
customa thick suspension is formed)
filtrationthe product is filtered off
washwashed with isopropanol and hexane

Sources & evidence

ORD record: ord-1ddbbc99da6a4b91a7da37458ff21310
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180636B2

Reaction notes

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