Ethylene Glycol → HCID 11289861, compound

HRID 254168Notes

Reaction equation

HRID 254168 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](Br)[N:13]=2)=[O:9])[CH:5]=[C:4]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1.[NH4+:24].[OH-].C(O)CO.O>Cl.[Cu-]=O>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:24])[N:13]=2)=[O:9])[CH:5]=[C:4]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 14923Ammonium HydroxideHCID 11303329HCID 11303329, compound

Product 1

HCID 11289861HCID 11289861, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-N-(6-bromo-2-pyridylmethyl)-6-(2-furyl)pyrimidine-4-carboxamide (350 mg, 0.93 mmol) and copper(I)oxide (6.7 mg, 0.046 mmol) in 4-M NH4OH in ethylene glycol (20.23 ml, 80.92 mmol) was heated in a sealed tube at 90° C. for 20 h, cooled, poured into water (100 mL) and extracted with EtOAc (2×25 mL). The combined organic phase was washed with brine (10 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; Hexane:EtOAc (1:4)-(0:1)] to give the title compound (65 mg, 22%) as a cream solid.

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc (2×25 mL)
  3. washThe combined organic phase was washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography [SiO2; Hexane:EtOAc (1:4)-(0:1)]

Sources & evidence

ORD record
ord-659df1794c574daca8a4b51244b8fd0a
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

Loading…