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

HRID 369863

반응식

HRID 369863 반응식
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][C:4]=2[N:5]=[CH:6][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:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

5

반응물 3

HCID 79323-ChloroanilineHCID 21262606Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylateHCID 21585144Isopropanol hexane

생성물 1

HCID 212626224-(3-chloroanilino)-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

Under an argon atmosphere, 29.0 g (128 mmol) of 4-chloro-6-ethoxycarbonyl-7H-pyrrolo[2,3-d]pyrimidine and 18.0 ml (171 mmol) of 3-chloro-aniline in 430 ml of n-butanol are stirred at 100° C. for 3 hours (almost dissolved after ≈1 hour, then a thick suspension forms). The reaction mixture is cooled to ~50° C., then 400 ml of isopropanol/hexane (1:1) are added thereto. The reaction mixture is then cooled to RT and the product is filtered off and washed with isopropanol and hexane. Stirring from diethyl ether yields the title compound: 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).

후처리

  1. dissolutionalmost dissolved after ≈1 hour
  2. temperatureThe reaction mixture is cooled to ~50° C.
  3. filtrationthe product is filtered off
  4. washwashed with isopropanol and hexane

출처 및 근거

ORD 기록
ord-e6cf8974b0ed425bb3de8a192aa716e7
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140332

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