Triethylamine → HCID 14814204, compound

HRID 1089272Notes

Reaction equation

HRID 1089272 reaction equation
Cl[C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]=[C:4]([NH:12][CH:13]=[O:14])[N:3]=1.[CH3:15][C:16]1([CH3:24])[O:20][C@@H:19]([CH2:21][O:22][NH2:23])[CH2:18][O:17]1.C(N(CC)CC)C>O1CCOCC1>[Cl:11][C:6]1[C:7]([NH:8][CH:9]=[O:10])=[C:2]([NH:23][O:22][CH2:21][C@H:19]2[CH2:18][O:17][C:16]([CH3:24])([CH3:15])[O:20]2)[N:3]=[C:4]([NH:12][CH:13]=[O:14])[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11298047(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineHCID 13989892N-(4,6-dichloro-2-formamido-pyrimidin-5-yl)formamide

Product 1

HCID 14814204HCID 14814204, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (3.5 g, 15 mmol), (R)-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)amine (2.65 g, 18 mmol) and triethylamine (20 ml, 150 mmol) in dioxan (80 ml) was stirred at 100° C. for 4 hours. The reaction was cooled, filtered and evaporated under reduced pressure. The residue was chromatographed on silica, eluting with chloroform-methanol (10:1), affording slightly impure (R)-4-chloro-2,5-diformamido-6-(2,2-dimethyl-1, 3-dioxolan-4-ylmethoxyamino)pyrimidine (1.05 g, 20%) as pale orange solid. IR: υmax (nujol) 3400, 3300, 3180, 1690, 1650 cm-1 ;

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customThe residue was chromatographed on silica
  5. washeluting with chloroform-methanol (10:1)

Sources & evidence

ORD record
ord-ff2da060931e43eb81ef9a3544a0c292
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

Loading…