Triethylamine → 6-[[3-Acetoxy-2-(diethoxyphosphorylmethoxy)propoxy]amino]-4-chloro-5-formamidopyrimidine

HRID 6248Notes

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.[C:12]([O:15][CH2:16][CH:17]([CH2:28][O:29][NH2:30])[O:18][CH2:19][P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])(=[O:14])[CH3:13].C(N(CC)CC)C>O1CCOCC1>[C:12]([O:15][CH2:16][CH:17]([O:18][CH2:19][P:20]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:27])[CH2:28][O:29][NH:30][C:6]1[N:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[NH:8][CH:9]=[O:10])(=[O:14])[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4,6-dichloro-5-formamidopyrimidine (0.77 g, 4.0 mmol), diethyl [2-acetoxy-1-(aminooxymethyl)ethoxy]methylphosphonate (1.2 g, 4.0 mmol) and triethylamine (0.82 ml, 6 mmol) in dry dioxan (20 ml) was heated at 100° C. for 2 hours. The reaction mixture was cooled, filtered, and the filtrate evaporated to leave an oil which was chromatographed on silica gel (eluant dichloromethane:methanol 97:3) and gave the title compound as a yellow oil (1.08 g, 60%). 1H NMR: δH [(CD3)2SO] 1.23 (6H,t, J=7 Hz, (OCH2CH3)2), 2.03 (3H,s, COCH3), 3.85-4.35 (11H,m, (OCH2CH3)2 +OCH2P+OCH2CHCH2O). m/z: observed 454.1020; C15H24N4O8PCl (M+) requires 454.0996.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered
customthe filtrate evaporated
customto leave an oil which
customwas chromatographed on silica gel (eluant dichloromethane:methanol 97:3)

Sources & evidence

ORD record: ord-1ecd3089eefd43c196a7041c766f44e5
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05247085

Reaction notes

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