2-Chloroethyl methyl sulfide → 6-Methoxy-7-(2-methylthioethoxy)4-phenoxyquinazoline

HRID 634695Notes

Reaction equation

[CH3:1][S:2][CH2:3][CH2:4]Cl.[OH:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[O:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:25][O:24][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:7]=1[O:6][CH2:4][CH2:3][S:2][CH3:1])[N:14]=[CH:13][N:12]=[C:11]2[O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 110 °C

Procedure

2-Chloroethyl methyl sulphide (1.2 g, 10.9 mmol) was added to 7-hydroxy-6-methoxy-4-phenoxyquinazoline (2.25 g, 8.4 mmol), (prepared as described for the starting material in Example 16), and potassium carbonate (6.0 g, 43.4 mmol) in DMF (70 ml). The mixture was heated at 110° C. for 4 hours and allowed to cool. The mixture was filtered, and the volatiles were removed from the filtrate by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (96/4) to give 6-methoxy-7-(2-methylthioethoxy)4-phenoxyquinazoline (1.55 g, 54%).

Workup

custom(prepared
temperatureto cool
filtrationThe mixture was filtered
customthe volatiles were removed from the filtrate by evaporation
customThe residue was purified by column chromatography
washeluting with methylene chloride/methanol (96/4)

Sources & evidence

ORD record: ord-74b387d7a47b4748b60276a6261487fe
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184225B2

Reaction notes

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