Diisopropylethylamine → 4-Chloro-6-[3-(diethoxyphosphorylmethoxy)propoxyamino]-2,5-diformamidopyrimidine

HRID 345056Notes

Reaction equation

[NH2:1][O:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11].[Cl:16][C:17]1[C:22]([NH:23][CH:24]=[O:25])=[C:21](Cl)[N:20]=[C:19]([NH:27][CH:28]=[O:29])[N:18]=1.C(N(C(C)C)CC)(C)C>COCCOCCOC>[Cl:16][C:17]1[C:22]([NH:23][CH:24]=[O:25])=[C:21]([NH:1][O:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][P:8]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[O:15])[N:20]=[C:19]([NH:27][CH:28]=[O:29])[N:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of diethyl 3-aminooxypropoxymethylphosphonate (4 g,16.6 mmol), 4,6-dichloro-2,5-diformamidopyrimidine (3.9 g, 16.6 mmol) and diisopropylethylamine (8.67 ml, 49.8 mmol) in diglyme (80 ml) was heated at 100° C. for 2 h. After removal of the solvent under reduced pressure, the residue was chromatographed in chloroform/methanol (100:1, 50:1, 10:1) affording 4-chloro-6-[3-(diethoxyphosphorylmethoxy)propoxyamino]-2,5-diformamidopyrimidine as a yellow oil (4.61 g, 63%); νmax (film) 3200, 2990, 1690, 1590, 1220, 1040 cm-1 ; δH [(CD3)2SO] 1.22(6H, t, J7 Hz, (CH3CH2O)2), 1.85(2H, m, CH2CH2CH2), 3.65(2H, t, J6.3 Hz, CH2OCH2P), 3.40(2H, d, J8.2 Hz, CH2P), 3.92(2H, t, J6 Hz, CH2ON), 4.04(4H, m, (CH3CH2O)2), 8.15(1H, s, CHO), 9.25(1H, br.s, CHO), 9.43(1H, br.s, D2O exchangeable, NH), 10.76(1H, br s, D2O exchangeable, NH), 10.86(1H, br.s,D2O exchangeable, NH); Found: M+ 439.1015; C14H23ClN5O7P requires: M+ 439.1024.

Workup

customAfter removal of the solvent under reduced pressure
customthe residue was chromatographed in chloroform/methanol (100:1, 50:1, 10:1)

Sources & evidence

ORD record: ord-63bf1e86d22349b2989617393b198ba4
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05055458

Reaction notes

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