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

HRID 1358282노트

반응식

HRID 1358282 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-77e57b4f03ba49adae85a01882670360
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596726B1

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