tert-Butanol → HCID 21995254, compound

Participants

Reaction Steps

To a solution of diphenylphosphorylazide (0.92 ml, 4.3 mmol) in tert-butyl alcohol (10 ml), was added triethylamine (1,2 m, 8.5 mmol) and 4-carboxy-N-(3,4,5-trimethoxyphenyl)-2-pyrimidineamine (1.0 g, 2.9 mmol), [see Example 121] and the mixture heated at reflux for 2 h. After this time the solvent was evaporated and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was washed with water (100 ml), dried (MgSO4) and concentrated under reduced pressure. Column chromatography [silica 2% methanol CH2Cl2] gave the title compound (850 mg) as a light yellow solid m.p. 124°. δH (CDCl3) 8.27 (1H, d, J 5.8 Hz), 7.45 (1H, br s), 7.32 (1H, d, J 5.8 Hz), 7.20 (1H, br s), 6.81 (2H, s), 3.85 (6H, s), 3.81 (3H, s) and 1.53 (9H, s). MS m/z 377 (M+H)+.

Provenance & Evidence