1,1-Dichloroethane → HCID 59682928, compound

HRID 1668681Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[N:7]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].[Cl:29][CH:30](Cl)[CH3:31]>CN(C=O)C>[Cl:29][CH2:30][CH2:31][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[N:7]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:21][CH3:22]

Participants

Conditions

Temperature: 70 °C

Procedure

7-Hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (85 g, 270 mmol, several batches pooled together) was dissolved in DMF (400 mL), potassium carbonate (77 g, 550 mmol) and dichloroethane (400 mL, 5130 mmol) were added and the reaction mixture was stirred overnight at 70° C. The solid was removed by filtration and washed with DMF. The solvent was evaporated and the solid so obtained was washed with water and dried at 50° C. over P2O5. The crude product was purified by flash chromatography using dichloromethane/ethyl acetate (85/15 up to 75/25). Evaporation of the solvent gave 7-(2-chloroethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (65.6 g, 66%) as a white solid.

Workup

customThe solid was removed by filtration
washwashed with DMF
customThe solvent was evaporated
customthe solid so obtained
washwas washed with water
dry with materialdried at 50° C. over P2O5
customThe crude product was purified by flash chromatography
customEvaporation of the solvent

Sources & evidence

ORD record: ord-3e5127264c1d4821992d38a585a2912b
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989460B2

Reaction notes

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