Water → 6-Chloro-8-oxa-3,5-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),3,5,10,12-hexaene

HRID 1358303Notes

Reaction equation

CN(C=O)C.[C:6](Cl)([C:8]([Cl:10])=O)=[O:7].[N:12]1[C:17]2[C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3OC=2C(=O)[NH:14][CH:13]=1.O>ClCCCl>[Cl:10][C:8]1[C:6]2[O:7][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[C:17]=2[N:12]=[CH:13][N:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

DMF (0.23 mL, 3.1 mmol) is added dropwise to a solution of (COCl)2 (0.28 mL, 3.1 mmol) in 1,2-dichloroethane (15 mL) at 25° C. After gas evolution ceases, 3H-benzofurano[3,2-d]pyrimid-4-one (113 mg, 0.61 mmol) is added. The resulting mixture is heated at reflux for 1 h. After the reaction has cooled to 25° C., water is added and the resulting mixture is extracted with CHCl3. The combined extracts are washed with water, saturated brine and dried (MgSO4). The solvent is removed under reduced pressure to give 4-chlorobenzofurano[3,2-d]pyrimidine (116 mg, 93%) as a yellow solid. 1H NMR (DMSO) δ9.08 (1H, s), 8.30 (1H, d. J=8.1 Hz), 8.02 (1H, d, J=8.5 Hz), 7.90, (1H, dt, Jd=1.3 Hz, Jt=7.1 Hz), 7.64 (1H, dt, Jd=1.0 Hz, Jt=7.8 Hz).

Workup

temperatureThe resulting mixture is heated
temperatureat reflux for 1 h
extractionthe resulting mixture is extracted with CHCl3
washThe combined extracts are washed with water, saturated brine
dry with materialdried (MgSO4)
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-43e66aa188b24f6e9f1aeb47108eae7d
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06596726B1

Reaction notes

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