Phosphorus oxychloride → HCID 54978103、化合物

HRID 1056837

反応式

HRID 1056837 の反応式
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[C:6](O)[C:7]2[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C:11]=3[S:10][C:8]=2[N:9]=1.C([O-])(O)=O.[Na+].O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:6]1[C:7]2[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C:11]=3[S:10][C:8]=2[N:9]=[C:4]([CH2:3][O:2][CH3:1])[N:5]=1

参加物

4

反応物 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178494690HCID 178494690、化合物

生成物 1

HCID 54978103HCID 54978103、化合物

反応条件

温度
92.5 °C

実験手順

A stirring suspension of 2-Methoxymethyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-ol (2.0 g, 0.008 mol) in POCl3 (20 ml) was heated to 90-95° C. for 4 h and progress was monitored by TLC. After completion of reaction, excess of POCl3 was distilled off to get oily mass which was poured onto ice-water solution (200 ml) and basified with saturated solution of NaHCO3 to pH ˜8. The aqueous phase was extracted well with ethyl acetate (2×250 ml). Combined organic layers were washed with brine solution (100 ml), dried over anhydrous Na2SO4 and concentrated in vacuo to get brown colored crude compound 4-Chloro-2-methoxymethyl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine which was forwarded as such for the next step reaction. Yield: (2 g, 93%); 1H NMR (400 MHz, CDCl3) δ ppm=4.60 (s, 2H), 3.37 (s, 3H), 3.00-2.99 (m, 2H), 2.88 (m, 2H), 1.85-1.83 (m, 4H); LCMS: [M+H]=269.1.

後処理

  1. customAfter completion of reaction
  2. distillationexcess of POCl3 was distilled off
  3. customto get oily mass which
  4. additionwas poured onto ice-water solution (200 ml)
  5. extractionThe aqueous phase was extracted well with ethyl acetate (2×250 ml)
  6. washCombined organic layers were washed with brine solution (100 ml)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6cd4924e8c1a4a6a9bc9eabf4388a6aa
出典データセット
uspto-grants-2016_07
特許番号
US09399647B2

関連ノート

読み込み中…