Hydrochloric Acid → 6-chloro-5-methyl-N-phenylpyrimidin-4-amine

HRID 241004

반응식

HRID 241004 반응식
Cl[C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(O)(C)C>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[CH3:8]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8188604,6-Dichloro-5-methylpyrimidine

생성물 1

HCID 637349086-chloro-5-methyl-N-phenylpyrimidin-4-amine수율 85.1%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a mixture of 4,6-dichloro-5-methylpyrimidine (2.27 g, 13.9 mmol) and aniline (1.0 g, 10.7 mmol) in isopropanol (15 mL) was added concentrated aqueous hydrochloric acid (1.5 mL) and heated to reflux for 2.5 h. The mixture was then concentrated and the residue triturated with ethyl acetate:isopropanol 4:1. The solid was collected by filtration and washed with additional ethyl acetate:isopropanol 4:1 then dried to give 6-chloro-5-methyl-N-phenylpyrimidin-4-amine (2.0 g, 67% yield). 1H NMR (400 MHz, d6-DMSO): 8.85 (s, 1H), 8.26 (s, 1H), 7.60 (d, 2H), 7.35 (tr, 2H), 7.11 (tr, 1H), 2.31 (s, 3H). MS (EI) for C11H10ClN3: 220 (MH+).

후처리

  1. temperatureheated
  2. temperatureto reflux for 2.5 h
  3. concentrationThe mixture was then concentrated
  4. customthe residue triturated with ethyl acetate:isopropanol 4:1
  5. filtrationThe solid was collected by filtration
  6. washwashed with additional ethyl acetate:isopropanol 4:1
  7. customthen dried

출처 및 근거

ORD 기록
ord-22761ad4d6464744adf8f3738e887d43
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648066B2

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