Reacción #6059

Ecuación de reacción

triethylamine

2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1- dimethylethyl)diphenyl-silyl)oxymethyl)-1-aminocyclobutane

product

2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1-dimethylethyl)-diphenylsilyl)oxymethyl)-1-aminocyclobutane

Diethyl ether

2-amino-6-chloro-4-hydroxy-5-nitropyrimidine

→

title compound

Rendimiento 64.0%

2-Amino-4-hydroxy-5-nitro-6-(2'-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3'-(((1,1-dimethylethyl)diphenylsilyl)oxymethyl)cyclobutylamino)pyrimidine

Rendimiento 64.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe ether solution was washed with 2×50 mL of water
2. 2
   Secadodried over anhydrous magnesium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue (800 mg) was dissolved in methylene chloride
6. 6
   Otropurified on a 1.0×45 cm silica gel column
7. 7
   Lavadoeluted @ 10 psi with 100 mL of methylene chloride

Procedimiento

2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1- dimethylethyl)diphenyl-silyl)oxymethyl)-1-aminocyclobutane (588 mg, 0.99 mmol), the product of Step N, 189 mg (0.99 mmol) of 2-amino-6-chloro-4-hydroxy-5-nitropyrimidine (prepared as described by J. F. Constant, et al. in J. Heterocyclic Chem, 1035 (1985)) and triethylamine (220 μL, 1.50 mmol) were combined in 5 mL of anhydrous DMF. The reaction mixture was stirred in an oil bath at 50° C. under a nitrogen atmosphere for 2.5 h. Diethyl ether (200 mL) was added and the ether solution was washed with 2×50 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue (800 mg) was dissolved in methylene chloride and purified on a 1.0×45 cm silica gel column eluted @ 10 psi with 100 mL of methylene chloride, followed by 100 mL of 2% methanol in methylene chloride and finally 100 mL of 4% methanol in methylene chloride, to give 473 mg (64% yield) of the title compound; MS DCI-NH3M/Z: 748 (M+H)+ ; 1H NMR (CDCl3) δ 2.13-2.33 (m, 3H), 2.89 (s, 1H), 2.97 (s, 1H), 3.59-3.70 (m, 2H), 4.26 (t, 1H), 4.65 (m, 1H), 7.30-7.47 (m, 10H), 7.56-7.60 (m, 10H).

Fuente