4-Chloro-6,7-dimethoxy-2-methylquinazoline → HCID 86698302, compound

HRID 2408989Notes

Reaction equation

HRID 2408989 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([CH3:16])[N:3]=1.[NH2:17][C:18]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[Se:20][C:19]=1[C:27]([NH2:29])=[O:28].CN(C=O)C.[OH-].[Na+]>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[C:4]([CH3:16])[N:3]=[C:2]2[NH:17][C:18]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:24])[CH3:25])[Se:20][C:19]=1[C:27]([NH2:29])=[O:28]

Participants

4

Reactant 3

HCID 104901504-Chloro-6,7-dimethoxy-2-methylquinazolineHCID 86646889HCID 86646889, compoundHCID 86698281HCID 86698281, compound

Product 1

HCID 86698302HCID 86698302, compound

Procedure

The reaction of 4-chloro-6,7-dimethoxy-2-methylquinazoline with 3-amino-5-tert-butylselenophene-2-carboxamide in the presence of DMF/NaOH as described in Example 1 gave title compound as an off-white color solid, mp 266-268° C. 1H NMR (400 MHz, CDCl3): δ 11.95 (1H, br s, exchangeable with D2O), 8.97 (1H, s), 7.32 (1H, s), 7.19 (1H, s), 5.38 (2H, br s, exchangeable with D2O), 4.08 (3H, s), 4.01 (3H, s), 2.70 (3H, s), 1.47 (9H, s); 13C NMR (100 MHz, CDCl3): δ 168.63, 168.60, 162.1, 154.8, 154.5, 149.2, 148.2, 148.1, 121.9, 109.0, 107.4, 107.1, 100.1, 56.2, 56.1, 37.1, 32.5, 26.3; LC-MS (negative ion mode): m/z 445, 447 (M−H)−.

Sources & evidence

ORD record
ord-a5ce7105f4f74c7c9a9369bfee1aa132
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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