4-Chloro-6,7-dimethoxyquinazoline → HCID 15523629, compound

HRID 726584Notes

Reaction equation

[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([Sn](C)(C)C)=[CH:6]1)(=[O:4])=[O:3].Cl[C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=2)[N:22]=[CH:21][N:20]=1>CN(C)C=O.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[CH:6]1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 1.33 g (4.01 mmol) of N-methylsulfonyl-3-trimethylstannylindole, 750 mg (3.34 mmol) of 4-chloro-6,7-dimethoxyquinazoline and 0.19 g (5 mol % 0.16 mmol) of Pd (PPh3)4 in 10 ml of dry dimethylformamide is flushed thoroughly with nitrogen and heated to 90° C. for 12 hours. The reaction mixture is diluted with methylene chloride washed with 10% ammonium hydroxide and stirred vigorously and then washed with water and the combined organics are washed with brine (75 mL), dried (MgSO4) and evaporated to dryness. Recrystallized from ethyl acetate yields 4-(1-methylsulphonylindol-3-yl)-6,7-dimethoxyquinazoline (m.p. >220° C.).

Workup

washwashed with 10% ammonium hydroxide
washwashed with water
washthe combined organics are washed with brine (75 mL)
dry with materialdried (MgSO4)
customevaporated to dryness
customRecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-b37c80f51cab476ebdf7f75ef7c643db
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05710158

Reaction notes

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