Acetonitrile → 4-Pyrimidinecarbonitrile,2-amino-6-(2-furanyl)-5-methyl-

HRID 254169

Reaction equation

HRID 254169 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([NH2:14])[N:3]=1.[C:15](#[N:17])C>>[NH2:14][C:4]1[N:3]=[C:2]([C:15]#[N:17])[C:7]([CH3:8])=[C:6]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:5]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 185072434-Chloro-6-(2-furyl)-5-methylpyrimidine-2-amine

Product 1

HCID 668471164-Pyrimidinecarbonitrile,2-amino-6-(2-furanyl)-5-methyl-Yield 65%

Conditions

Temperature
140 °C

Procedure

A solution of 4-chloro-6-(2-furyl)-5-methylpyrimidine-2-amine (80 mg, 0.38 mmol) in acetonitrile (4 mL) was treated with polymer supported cyamide (0.636 mg, 1.91 mmol), stirred at 140° C. in the microwave for 30 min, filtered to remove the resin and the filter cake washed with acetonitrile. The filtrate was concentrated in vacuo to give the title compound (50 mg, 65%) as off-white solid; NMR δH (400 MHz, DMSO) 2.48 (3H, s), 6.75 (1H, dd, J 1.7, 3.5 Hz), 7.04 (2H br s), 7.28 (1H, dd, J 0.7, 3.5 Hz) and 8.00 (1H, dd, J 0.7, 1.7 Hz); M/Z 201 (M=H)+; HPLC 1.1 min. (50/80).

Workup

  1. filtrationfiltered
  2. customto remove the resin
  3. washthe filter cake washed with acetonitrile
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c74d9c1988604ab2acf5b2d783e0e5bb
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Linked notes

Loading…