N,N-Diethylaniline → 7-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 8714

反応式

HRID 8714 の反応式
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](=O)[NH:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:32]>>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([Cl:32])=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 1357235075,6,7,8-Tetrahydro-7-(phenylmethyl)pyrido(3,4-d)pyrimidin-4(3H)-one

生成物 1

HCID 219588387-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

反応条件

温度
80 °C

実験手順

To a mixture of 7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one 3a (1.0 g, 4.14 mmol) and N,N-diethylaniline (0.37 g, 2.48 mmol) was slowly added POCl3 (12 mL). The mixture was heated to 80° C. for 20 h. After evaporation of the excess of POCl3, the residue was poured into ice, dichloromethane was added and the mixture was made basic (pH=11) with solid Na2CO3. The product was extracted with dichloromethane, dried, and concentrated. Flash column chromatography with 20% ethyl acetate:hexane gave 0.46 g of 7-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidine 4a as a yellow oil.

後処理

  1. customAfter evaporation of the excess of POCl3
  2. additionthe residue was poured into ice, dichloromethane
  3. additionwas added
  4. extractionThe product was extracted with dichloromethane
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d8649f47a7b846b880d52e1adecdf85c
出典データセット
uspto-grants-2006_08
特許番号
US07091200B2

関連ノート

読み込み中…