Methyl chloroformate → HCID 11508604, compound

HRID 1668798Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]=[C:5]2[N:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:14].C(=O)([O-])[O-].[K+].[K+].Cl[C:30]([O:32][CH3:33])=[O:31]>C1COCC1.CCOC(C)=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>[CH3:33][O:32][C:30]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]=[C:5]2[N:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:14])=[O:31]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (6-amino-2-methyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methylamine (150 mg, 0.51 mmol) in 5 ml of THF was added potassium carbonate (160 mg, 1.16 mmol), 2 mg of sodium sulfate. The reaction mixture was cooled to 0° C., and methyl chloroformate (0.4 ml, 5 mmol) was added. The reaction mixture was stirred at 0° C. for 10-15 min, then diluted with EtOAc (20 ml), washed with water, brine, dried over Na2SO4, filtered and concentrated by vacuum. The crude product was purified by chromatography on silica gel with acetate, hexane (1:3 to 1:1) as eluent, yielding 129 mg of title compound (72%) as yellow solids. 1H NMR (CDCl3): 7.70 (s, 2H), 7.12-7.07 (m, 2H), 6.94-6.89 (m, 3H), 6.32 (brs, 1H), 3.84 (s, 3H), 3.70 (s, 3H), 3.57 (s, 3H), 2.70 (s, 3H).

Workup

washwashed with water, brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated by vacuum
customThe crude product was purified by chromatography on silica gel with acetate, hexane (1:3 to 1:1) as eluent

Sources & evidence

ORD record: ord-ee00946a4d494bc3bb232704161a77c4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989462B2

Reaction notes

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