Water → 2-Amino-6-(2-furyl)pyrimidine-4-carbonitrile

HRID 254152Notes

Reaction equation

HRID 254152 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1.[Na].[N:15]12CCN(CC1)C[CH2:16]2.O>CS(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([C:16]#[N:15])[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9237Dabco2×HCID 5360545SodiumHCID 223243064-Chloro-6-(2-furanyl)-2-pyrimidinamine

Product 1

HCID 668464412-Amino-6-(2-furyl)pyrimidine-4-carbonitrileYield 762.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 2-amino-4-chloro-6-(2-furyl)pyrimidine (9.78 g, 50.0 mmol) in DMSO (200 mL) was treated with sodium cyamide (14.7 g, 300 mmol) and 1,4-diazabicyclo[2.2.2]octane (DABCO) (0.56 g, 5.0 mmol). The suspension was stirred for 4 days, and more DABCO (5.04 g, 45 mmol) and DMSO (100 mL) were added. The suspension was stirred for a further 2 days, poured onto a mixture of ice (750 g) and water (750 mL), the crude product was filtered off, washed with water and MeCN, and dried in air to give the title compound (7.1 g, 77%) as a brown solid; m.p. 193-194° C.; NMR δH (400 MHz, DMSO) 6.74 (1H, q, J 1.6 Hz), 7.32 (2H, br s), 7.39 (1H, d, J 3.6 Hz), 7.43 (1H, s) and 7.98 (1H, d, J 1.2 Hz); M/Z 187 (M+H)+.

Workup

  1. stirringThe suspension was stirred for a further 2 days
  2. filtrationthe crude product was filtered off
  3. washwashed with water and MeCN
  4. customdried in air

Sources & evidence

ORD record
ord-1f3484034b8a470c9a3bcc701089f92f
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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