Trimethylamine → HCID 19392528, compound

HRID 1755993Notes

Reaction equation

HRID 1755993 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:4][N:3]=1.[CH3:14][N:15](C)C>C1(C)C=CC=CC=1>[C:14]([C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:4][N:3]=1)#[N:15]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 19392531HCID 19392531, compound

Product 1

HCID 19392528HCID 19392528, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 2-chloro-4-(2,2,2-trifluoroethoxy)-pyrimidine (142 g) in toluene (330 ml) was added to trimethylamine (140 ml of a 45% aqueous solution) at 0° C. After stirring for 16 hours the organic phase was separated off. The aqueous phase was added to toluene (330 ml) then a solution potassium cyanide (44 g in 170 ml water) was added at 0° C. The reaction mixture was stirred for a further 16 hours and then the organic phase was separated, the aqueous was extracted with ether (2×200 ml) and the combined organic extracts were dried and concentrated to give 2-cyano-4-(2,2,2-trifluoroethoxy)-pyrimidine (73.5 g, 77% yield) as a yellow oil; 1H NMR (270 MHz): δ4.85(2H,q), 7.10(1H,d), 8.64(1H,d) ppm.

Workup

  1. customwas separated off
  2. additionThe aqueous phase was added to toluene (330 ml)
  3. additiona solution potassium cyanide (44 g in 170 ml water) was added at 0° C
  4. stirringThe reaction mixture was stirred for a further 16 hours
  5. customthe organic phase was separated
  6. extractionthe aqueous was extracted with ether (2×200 ml)
  7. customthe combined organic extracts were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f7db772c172f4dcfb872d560f16605a9
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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