Triethylamine → 4-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-5-formamidopyrimidine

HRID 373882Notes

Reaction equation

HRID 373882 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH2:12][O:13][CH2:14][CH2:15][CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20].C(N(CC)CC)C>O1CCOCC1>[Cl:1][C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6]([NH:12][O:13][CH2:14][CH2:15][CH2:16][P:17]([O:18][CH2:19][CH3:20])([O:21][CH2:22][CH3:23])=[O:24])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10932261N-(4,6-dichloropyrimidin-5-yl)formamideHCID 19808651Diethyl 3-(aminooxy)propylphosphonate

Product 1

HCID 198086534-Chloro-6-[[3-(diethoxyphosphoryl)propoxy]amino]-5-formamidopyrimidineYield 82.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4,6-dichloro-5-formamidopyrimidine (2.82 g, 14.6 mmol), diethyl 3-(aminooxy)propylphosphonate (3.1 g, 14.6 mmol) and triethylamine (3.1 ml, 22.3 mmol) in dioxan (40 ml) was heated at 100° C. for 4 hours. The solution was cooled to ambient temperature, filtered, and the filtrate evaporated to give a yellow oil. The oil was purified by column chromatography on silica gel (eluting with chloroform: methanol 97:3) to give the title compound as a yellow oil (4.4 g, 74%). 1H NMR: δH (CDCl3) 1.3 (6H, t, J=7Hz, (OCH2CH3)2), 1.6-2.5 (4H, m, CH2CH2P), 3.9-4.5 (6H, m, N--OCH2, (OCH2CH3)2), 7.3-9.3 (3H, broad, --NHCHO, --NH--OCH2).

Workup

  1. temperatureThe solution was cooled to ambient temperature
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. customto give a yellow oil
  5. customThe oil was purified by column chromatography on silica gel (eluting with chloroform: methanol 97:3)

Sources & evidence

ORD record
ord-c054f13e5b37425e9f917ac3b204584e
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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