4-Methylmorpholine → HCID 178442253, compound

Participants

Reaction Steps

A mixture of 270 mg (1 eq) of 4-[5-(2,6-diamino-4-hydroxypyrimidin-5-yl)-pent-1-en-2-yl]benzoic acid and 104 mg (1.2 eq) of N-methylmorpholine in 4.0 ml of anhydrous tetrahydrofuran, was vigorously stirred for 5 minutes at room temperature. To this mixture, 165 mg (1.1 eq) of 2,4-dimethoxy-6-chloro-1,3,5-triazine were added and the sol was stirred for 40 minutes at room temperature. An additional 104 mg (1.2 eq) of N-methylmorpholine were introduced followed by 236 mg (1.3 eq) of dry dimethyl-L-glutamate hydrochloride. The solution then was continuously stirred for 4 hours at room temperature. The solvent was removed under reduced pressure and the residue dissolved in chloroform. Extraction with saturated aqueous sodium bicarbonate removed unreacted acid, triazine and triazinone. The organic layer was dried over magnesium sulfate, filtered and evaporated to dryness to yield the product which was further purified by flash chromatography eluting with 1:10 methanol:chloroform. M.S.:m/z=471.2081 (M+, calc. for C23H29N5O6 : 471.2118). 1H-N.M.R. (CDCl3, 300 MHz): 1.41(quin, 2H, CH2 --CH2 --CH2, J=7.5 Hz); 2.00-2.55(m, 8H, 4×--CH2 --); 3.56(s, 3H, CH3O); 3.68(s, 3H, CH3O); 4.68 (dt, 1H, CH, J=6, 7.5 Hz); 4.84 (s (broad), 2H, NH2); 4.97 (s, 1Holef.); 5.18 (s, 1Holef.); 5.86 (s (broad), 2H, NH2); 7.29 (d, 2Harom., J=9 Hz); 7.62 (m, (broad), 1H, NHglu); 7.64 (d, 2Harom., J=9 Hz); 11.20 (s (broad), 1H, NHpyr).

Provenance & Evidence