HCID 14814204, compound → HCID 14814207, compound

HRID 1089273Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH:8][CH:9]=O)=[C:6]([NH:11][O:12][CH2:13][C@H:14]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]2)[N:5]=[C:4]([NH:21][CH:22]=[O:23])[N:3]=1>C(OC(OCC)OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][CH:22]=[O:23])[N:5]=[C:6]2[C:7]=1[N:8]=[CH:9][N:11]2[O:12][CH2:13][C@H:14]1[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (R)-4-chloro-2,5-diformamido-6-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxyamino)pyrimidine 11 (900 mg, 2.6 mmol) in diethoxymethyl acetate (20 ml) was stirred at 120° C. for 3 hours. The solvent was removed under reduced pressure, the residue dissolved in methanol (20 ml) containing 0.88 ammonia solution (0.5 ml) and the mixture stirred for 1 hour at 25° C. The solvents were evaporated under reduced pressure and the residue chromatographed on silica, eluting with ethyl acetate-hexane (2:1), affording (R)-6-chloro-9-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)-2-formamidopurine (530 mg, 62%), m.p. 145°-8° C. UV: λmax (MeOH) 232 (ε 26,800), 291 (ε 9,600)nm; 1R: υmax (nujol) 1700, 1600, 1580 cm-1 ; 1H NMR: δH (CDCl3) 1.37 (3H,s, CH3), 1.42 (3H s, CH3), 3.87 (1H, m, CH2OC), 4.12 (1H, m, CH2OC), 4.46 (3H, m, CH+CH2ON), 8.20 (1H, s, H-8), 8.44 (1H, br. d, J=11.5 Hz, D2O exchangeable, NH), 9.55 (1H, J=11.5 Hz, HCONH).

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue dissolved in methanol (20 ml)
additioncontaining 0.88 ammonia solution (0.5 ml)
customThe solvents were evaporated under reduced pressure
customthe residue chromatographed on silica
washeluting with ethyl acetate-hexane (2:1)

Sources & evidence

ORD record: ord-541fb49963044f6db903bdd473842b1f
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04965270

Reaction notes

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