Sodium ethoxide → (6-Bromo-4-ethoxy-quinazolin-2-yl)-methyl-amine

HRID 1783633Notes

Reaction equation

[O-:1][CH2:2][CH3:3].[Na+].[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:16][CH3:17])[N:10]=[C:9]2Cl>>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:16][CH3:17])[N:10]=[C:9]2[O:1][CH2:2][CH3:3]

Participants

Reactant 2

HCID 2723922Sodium ethoxide

HCID 57590623(6-Bromo-4-chloro-quinazolin-2-yl)-methyl-amine

Product 1

HCID 57590621(6-Bromo-4-ethoxy-quinazolin-2-yl)-methyl-amineYield 29.8%

Procedure

To a solution of sodium ethoxide (8.11 g, 119.3 mmol) in absolute alcohol (150 mL) was added powder (6-bromo-4-chloro-quinazolin-2-yl)-methyl-amine (13 g, 47.7 mmol) in one portion and the mixture was stirred for 3 hours at room temperature under N2 atmosphere. The excess of alcohol was removed in vacuo and the residue was purified by column to afford (6-bromo-4-ethoxy-quinazolin-2-yl)-methyl-amine (4 g, 14.2 mmol, 29.8%) as a light yellow solid. 1H NMR (DMSO-d6): δ 7.90-7.89 (d, 1H), 7.70-7.67 (dd, 1H), 7.33-7.31 (m, 1H), 7.21-7.20 (dd, 1H), 4.45-4.44 (q, 2H), 2.83-2.82 (d, 3H), 1.40-1.37 (t, 3H).

Workup

customThe excess of alcohol was removed in vacuo
customthe residue was purified by column

Sources & evidence

ORD record: ord-f060ebdb7bd541b3a7c86c1fbdefc008
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501428B2

Reaction notes

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