Ethanol → HCID 86066724, compound

HRID 254179Notes

Reaction equation

HRID 254179 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[O:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[N:3]=1.[CH3:15][NH2:16].CCO>CO>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[O:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[N:3]=[C:2]([NH:16][CH3:15])[N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 65712481HCID 65712481, compound

Product 1

HCID 86066724HCID 86066724, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2,4-dichloro-6-(5-methylfuran-2-yl)pyrimidine (0.70 g, 3.07 mmol) in MeOH (5 mL) was treated with 2-M methylamine in EtOH (2 mL, 4 mmol), heated at 80° C. for 30 min, cooled, concentrated in vacuo and purified by chromatography [SiO2; hexane:EtOAc (100:0-90:10)] to give the title compound (0.17 g, 22%) as a white solid; NMR δH (400 MHz, CD3OD) 2.38 (3H, s), 2.93 (3H, s), 6.22-6.23 (1H, m), 6.83 (1H, s) and 7.12-7.13 (1H, m); M/Z 224, 226 (M+H)+

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. custompurified by chromatography [SiO2; hexane:EtOAc (100:0-90:10)]

Sources & evidence

ORD record
ord-9edcc784757c414980a6ff0248ed9746
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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