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

HRID 1692994

反応式

HRID 1692994 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-db122cca4b324e5f8aba037e2860f8ef
出典データセット
uspto-grants-2012_04
特許番号
US08158641B2

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