6-Benzyloxyamino-4-chloro-2,5-diformamidopyrimidine → 9-Benzyloxy-6-chloro-2-formamidopurine

HRID 6254

Reaction equation

[CH2:1]([O:8][NH:9][C:10]1[N:15]=[C:14]([NH:16][CH:17]=[O:18])[N:13]=[C:12]([Cl:19])[C:11]=1[NH:20][CH:21]=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][N:9]1[CH:21]=[N:20][C:11]2[C:10]1=[N:15][C:14]([NH:16][CH:17]=[O:18])=[N:13][C:12]=2[Cl:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

6-Benzyloxyamino-4-chloro-2,5-diformamidopyrimidine (1.2 g, 3.73 mmol) and diethoxymethyl acetate (20 ml) was stirred at 120° C. for 2.5 hours, cooled and evaporated under reduced pressure. A solution of the residue in methanol (20 ml) and 0.880 ammonia (2 ml) was stirred at 20° C. for 1 hour, the solvent removed under reduced pressure and the residue co-evaporated with methanol. Column chromatography on silica gel (eluted with chloroform-ethanol, 100:1) afforded the title compound (700 mg, 62%). IR: νmax (KBr) 3119, 1702, 1611, 1577, 1505, 1440 cm-1 ; 1H NMR: δH [(CD3)2SO], 5.44 (2H, s, CH2Ph), 7.45 (5H, m, Ph), 8.54 (1H, s, H-8), 9.34 (1H, s, CHO), 11.30 (1H, br.s, D2O exchangeable, NH). Found: C, 49.99; H, 3.37; N, 22.43%, m/z 303.0523. C13H10N5O2Cl+0.5 H2O requires: C, 49.92; H, 3.55; N, 22.40%, m/z 303.0520.

Workup

temperaturecooled
customevaporated under reduced pressure
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-3e75075e6e304267be1415e6af320c90
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05247085

Linked notes

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