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

HRID 1358282Notes

Reaction equation

HRID 1358282 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-77e57b4f03ba49adae85a01882670360
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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