HCID 13989893, compound → HCID 13989894, compound
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][NH:13][C:14]1[N:19]=[C:18]([NH:20][CH:21]=[O:22])[N:17]=[C:16]([Cl:23])[C:15]=1[NH:24][CH:25]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OC(OCC)OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][N:13]1[CH:25]=[N:24][C:15]2[C:14]1=[N:19][C:18]([NH:20][CH:21]=[O:22])=[N:17][C:16]=2[Cl:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
6-(3-Benzyloxyprop-1-oxyamino)-4-chloro-2,5-diformamido pyrimidine (4.3 g, 11.3 mmol) in diethoxymethyl acetate (40 ml) was heated at 120° C. for 2.5 hours. The mixture was then cooled and evaporated to a syrup. The residue was dissolved in methanol (40 ml) and concentrated aqueous ammonia (5 ml). The solution was then stirred for 30 minutes at 20° C., evaporated under reduced pressure and the residue co-evaporated with methanol. Column chromatography on silica gel (eluted with chloroform-methanol, 50:1) gave the title compound (3.93 g, 95%) IR: υmax 3120, 3080, 1700, 1615, 1580, 1500, 1435 cm-1. 1H NMR: δH (CDC3) 2.15 (2H, quintet, J=6 Hz, CH2CH2CH2), 3.75 (2H, t, J=6 Hz, CH2OCH2Ph), 4.55 (4H, m, CH2ON, CH2Ph), 7.40 (5H, m, Ph), 8.10 (1H, s, H-8), 8.40 (1H, d, J=10 Hz, D2O exchangeable, NHCHO), 9.60 (1H, d, J=10 Hz, NHCHO).