HCID 22160572, compound → HCID 22160551, compound

HRID 1089251Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH:10]([CH2:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[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][CH:10]([CH2:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[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]=1

Participants

Conditions

Temperature: 20 °C

Procedure

6-(3-Benzyloxy-2-benzyloxymethylprop-1-oxyamino)-4-chloro-2,5-diformamidopyrimidine (4.8 g, 9.6 mmol) and diethoxymethyl acetate (50 ml) was stirred at 120° C. for 1.5 hours, cooled and evaporated under reduced pressure. The residue in methanol (80 ml) and concentrated ammonia solution (2 ml) was stirred at 20° C. for 30 minutes, the solvent removed under reduced pressure and the residue co-evaporated with methanol. Column chromatography on silica gel (eluted with chloroform and then chloroform-ethanol, 50:1) afforded the title compound (4.11 g, 89%). IR: υmax (KBr) 3110, 2900, 2860, 1700, 1610, 1575, 1500, 1440 cm-1. 1H NMR: δH [(CD3)2SO] 2.40 (1H, quintet, J=6.1, 6.7 Hz, CH), 3.64 (4H, J=6.7 Hz, 2×CH2OCH2Ph), 4.50 (6H, m, CH2ON, 2×CH2Ph), 7.30 ( 10H, m, 2×CH2Ph), 9.36 (1H, s, OCHNH), 11.31 (1H, s, NHCHO). Found: C, 59.44; H, 5.09; N, 13.62%. C24H24N5O4Cl.0.5EtOH requires: C, 59.45; H, 5.40; N, 13.87%.

Workup

temperaturecooled
customevaporated under reduced pressure
customthe solvent removed under reduced pressure
washColumn chromatography on silica gel (eluted with chloroform

Sources & evidence

ORD record: ord-a80984ea764a4deab8983f206a9e6dd3
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965270

Reaction notes

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