Trimethylamine → HCID 19392518, compound

HRID 1755991Notes

Reaction equation

HRID 1755991 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1.[O-]CC.[Na+].Cl[C:16]1N=C(Cl)C=C[N:17]=1.CN(C)C.[C-]#N.[K+]>CCOCC.O>[C:16]([C:2]1[N:7]=[C:6]([O:8][CH2:9][CH3:10])[CH:5]=[CH:4][N:3]=1)#[N:17]

Participants

8

Reactant 5

HCID 1146TrimethylamineHCID 9032Potassium CyanideHCID 775312,4-DichloropyrimidineHCID 2723922Sodium ethoxideHCID 47372802-Chloro-4-ethoxypyrimidine

Product 1

HCID 19392518HCID 19392518, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-chloro-4-ethoxy pyrimidine (20 g from the reaction of 1 equivalent of sodium ethoxide with 2,4-dichloropyrimidine at 0°-5° C.) in ether (50 ml) was added to ice cooled trimethylamine (50 ml of a 30% aqueous solution). After stirring the mixture for 2 hours a solution of potassium cyanide (9.0 g) in water (50 ml) was added and the resulting mixture was stirred vigorously at room temperature. After 16 hours the reaction mixture was extracted with ether (3×50 ml) and the combined extracts were washed with brine, dried and concentrated to give 2-cyano-4-ethoxypyrimidine (14.6 g, 77% yield) as a pale yellow liquid which gradually crystallised (m.p. 35° C.); 1H NMR (270 MHz): δ1.42(3H,t), 4.49(2H,q), 6.89(1H,d), 8.49(1H,d) ppm.

Workup

  1. additionwas added to ice
  2. additionwas added
  3. extractionAfter 16 hours the reaction mixture was extracted with ether (3×50 ml)
  4. washthe combined extracts were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5aa22e08d57547c69a7a5ddf88c81099
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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