Dimethylformamide → 4-Chloro-9-methoxybenzo[4,5]thieno[3,2-d]pyrimidine

HRID 1358282ノート

反応式

HRID 1358282 の反応式
CN(C=O)C.C(Cl)(C([Cl:10])=O)=O.[CH3:12][O:13][C:14]1[C:19]2[C:20]3[N:21]=[CH:22][NH:23][C:24](=O)[C:25]=3[S:26][C:18]=2[CH:17]=[CH:16][CH:15]=1>ClCCCl>[Cl:10][C:24]1[C:25]2[S:26][C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([O:13][CH3:12])[C:19]=3[C:20]=2[N:21]=[CH:22][N:23]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 1355040769-methoxy-4-oxo-3H-benzothieno[3,2-d]pyrimidine

生成物 1

HCID 106107284-Chloro-9-methoxybenzo[4,5]thieno[3,2-d]pyrimidine収率 66.1%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

DMF (0.125 mL, 1.7 mmol) is added dropwise to a solution of (COCl)2 (0.15 mL, 1.68 mmol) in 1,2-dichloroethane (4.5 mL) at r.t. After gas evolution ceases, 9-methoxy-4-oxo-3H-benzothieno[3,2-d]pyrimidine (73.2 mg, 0.32 mmol) is added. The resulting mixture is heated at reflux for 4 hr. After the reaction is cooled to r.t., the black tar is filtered off. The filtrate is stripped to dryness and then mixed with water. A yellow solid forms and is collected via filtration. The solid is washed with water and air dried to give 4-chloro-9-methoxybenzothieno[3,2-d]pyrimidine (53 mg, 66%). 1H NMR (DMSO) δ9.17 (1H, s), 7.82-7.78 (2H, m), 7.3-7.2 (1H, m) , 4.06 (3H, s).

後処理

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 4 hr
  3. filtrationthe black tar is filtered off
  4. additionmixed with water
  5. filtrationA yellow solid forms and is collected via filtration
  6. washThe solid is washed with water and air
  7. customdried

出典と根拠

ORDレコード
ord-77e57b4f03ba49adae85a01882670360
出典データセット
uspto-grants-2003_07
特許番号
US06596726B1

反応ノート

読み込み中…