N,N-Dimethylaniline → 4-chloro-N-(3-(2-methylthiazol-4-yl)phenyl)pyrimidin-2-amine

HRID 1692994노트

반응식

HRID 1692994 반응식
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[C:9]([NH:13][C:14]3[NH:19][C:18](=O)[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:11][CH:12]=2)[N:6]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:5]3[N:6]=[C:2]([CH3:1])[S:3][CH:4]=3)[CH:8]=2)[N:19]=1

참가 물질

4

반응물 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 577809112-(3-(2-methylthiazol-4-yl)phenylamino)pyrimidin-4(3H)-one

생성물 1

HCID 577809104-chloro-N-(3-(2-methylthiazol-4-yl)phenyl)pyrimidin-2-amine수율 47%

실험 절차

To 2-(3-(2-methylthiazol-4-yl)phenylamino)pyrimidin-4(3H)-one, 11, (1.0 g, 3.5 mmol) and N,N-dimethyl-aniline (1 mL) is added phosphorus oxychloride (9.5 mL). The resulting mixture is heated to reflux for 15 minutes, cooled to room temperature and concentrated in vacuo. The residue is neutralized to pH 7 with 1M NaOH (aqueous). The organic layer is extracted with ethyl acetate (3×50 mL). The combined organic layers are dried (MgSO4) and concentrated in vacuo. The residue is purified over silica (5% EtOAc in hexanes) to afford 0.50 g (47% yield) of the desired compound. 1H NMR (DMSO-d6, 300 MHz): δ 2.73 (s, 3H), 6.98 (d, J=5.1 Hz, 1H), 7.37 (t, J=8.1 Hz, 1H), 7.57 (d, J=8.1 Hz, 1H), 7.72 (d, J=8.1 Hz, 1H), 7.83 (s, 1H), 8.25 (s, 1H), 8.46 (d, J=5.1 Hz, 1H), 10.08 (s, 1H). MS (ESI, pos. ion) m/z: 303 (M+1).

후처리

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 15 minutes
  3. concentrationconcentrated in vacuo
  4. extractionThe organic layer is extracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified over silica (5% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-db122cca4b324e5f8aba037e2860f8ef
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158641B2

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