Diisopropylethylamine → 4-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-2,5-diformamidopyrimidine

HRID 373875Notes

Reaction equation

Cl[C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]=[C:4]([NH:12][CH:13]=[O:14])[N:3]=1.[NH2:15][O:16][CH2:17][CH2:18][CH2:19][P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23].C(N(C(C)C)CC)(C)C>COCCOCCOC>[Cl:11][C:6]1[C:7]([NH:8][CH:9]=[O:10])=[C:2]([NH:15][O:16][CH2:17][CH2:18][CH2:19][P:20]([O:21][CH2:22][CH3:23])([O:24][CH2:25][CH3:26])=[O:27])[N:3]=[C:4]([NH:12][CH:13]=[O:14])[N:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (1.48 g, 6.3 mmol), diethyl 3-(aminooxy)propylphosphonate (1.33 g, 6.3 mmol), diisopropylethylamine (2.19 ml, 12.6 mmol) in diglyme (20 ml) was heated at 100° C. for 11/2 hours. After cooling, the solvent was removed under reduced pressure. The residue was chromatographed on silica gel (dichloromethane-methanol (97:3) as eluant) to give the title compound as a yellow foam (1.15 g, 58% based on recovered pyrimidine). 1H NMR: δH ((CD3)2SO+D2O) 1.21 (6H, t, J=7Hz, (OCH2CH3)2), 1.65-2.00 (4H, m, CH2CH2P), 3.85-4.05 (6H, m, N--OCH2, (OCH2CH3)2), 7.90+8.15 (1H, 5-NHCHO), 9.25 (2-NHCHO) Found: C, 38.12; H, 5.15; N, 16.25%. C13H21N5O6PCl requires: C, 38.10; H, 5.17; N, 17.09%.

Workup

temperatureAfter cooling
customthe solvent was removed under reduced pressure
customThe residue was chromatographed on silica gel (dichloromethane-methanol (97:3) as eluant)

Sources & evidence

ORD record: ord-430fbbfc0de743098f5ccec979fa9c6b
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166198

Reaction notes

Loading…