Hydrochloric Acid → 4-(4-Hydroxyanilino)-6-(2-chloro-5-methylanilino)pyrimidine

HRID 987549

반응식

HRID 987549 반응식
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[CH:12]=[C:11](Cl)[N:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:18]=1[NH2:19].Cl>C(O)CCC>[OH:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[CH:12]=[C:11]([NH:19][C:18]3[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:17]=3[Cl:16])[N:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 667702-Chloro-5-methylanilineHCID 180091284-(4-Hydroxyanilino)-6-chloropyrimidine

생성물 1

HCID 114615694-(4-Hydroxyanilino)-6-(2-chloro-5-methylanilino)pyrimidine수율 84%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

The title compound was prepared in a similar manner to that of Reference Example 4 from 4-(4-hydroxyanilino)-6-chloropyrimidine (Reference Example 5) by reaction with 2-chloro-5-methylaniline in butan-1-ol in the presence of catalytic concentrated hydrochloric acid. The mixture was heated at reflux for 18 hours, concentrated and the residue purified by column chromatography eluting with DCMN:MeOH: concentrated ammonia (94:5:1). Yield 84%. NMR: 2.26 (3H, s), 5.85 (1H, s), 6.68 (2H, d), 6.93 (1H, d), 7.19 (2H, d), 7.32 (1H, d), 7.46 (1H, s), 8.09 (1H, s), 8.44 (1H, s), 8.69 (1H, s), 9.11 (1H, s); m/z 327 (MH+).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated
  4. customthe residue purified by column chromatography
  5. washeluting with DCMN

출처 및 근거

ORD 기록
ord-dbb5a656396d4342825bdfb7d63b6930
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06632820B1

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