Triethylamine → HCID 19808606, compound

HRID 373889Notes

Reaction equation

HRID 373889 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.[Si:12]([O:19][CH2:20][CH:21]([O:32][NH2:33])[CH2:22][CH2:23][P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C>O1CCOCC1>[Si:12]([O:19][CH2:20][CH:21]([O:32][NH:33][C:6]1[N:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[NH:8][CH:9]=[O:10])[CH2:22][CH2:23][P:24]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])=[O:31])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10932261N-(4,6-dichloropyrimidin-5-yl)formamideHCID 21650354HCID 21650354, compound

Product 1

HCID 19808606HCID 19808606, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4,6-dichloro-5-formamidopyrimidine (0.73 g, 3.8 mmol), diethyl [4-(t-butyldimethylsilyloxy)-3-(aminooxy)butyl]phosphonate (1.35 g, 3.8 mmol) and triethylamine (0.78 ml, 5.7 mmol) in dioxan (20 ml) was heated at 90° C. for 3 hours. After cooling to ambient temperature, the mixture was filtered and the filtrate evaporated. The residue was chromatographed on silica gel using dichloromethane-methanol (98:2) as eluant to yield the title compound as a oil (0.56 g, 29). IR: υmax (film) 3180, 2940, 2870, 1690, 1635, 1250, 1030, 970, 830, 780 cm-1. 1H NMR: δH (CDCl3) 0.05 (6H, s, SiMe2), 0.9 (9H, s, SiBut), 1.3 (6H, t, J=7Hz, (OCH2CH3 )2), 1.6-2.3 (4H, m, CH2CH2P), 3.6-4.3 (7H, m, OCH2CH+(OCH2CH3)2), 7.3-10.05 (4H, broad, --NHCHO+--NHO+H-2).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe mixture was filtered
  3. customthe filtrate evaporated
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-df660efabfc64e22a97811d92f7e31b7
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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