Hydrochloric Acid → HCID 19392516, compound

HRID 1755994Notes

Reaction equation

HRID 1755994 reaction equation
C[Mg]Br.[C:4]([C:6]1[N:11]=[C:10]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:9]=[CH:8][N:7]=1)#N.Cl.[C:19](=O)(O)[O-].[Na+].[OH2:24]>CCOCC.C1COCC1>[C:4]([C:6]1[N:11]=[C:10]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[CH:9]=[CH:8][N:7]=1)(=[O:24])[CH3:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 19392528HCID 19392528, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 19392516HCID 19392516, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Methyl magnesium bromide (115 ml of a 3.0M solution in ether) was added to 2-cyano-4-(2,2,2-trifluoroethoxy)-pyrimidine (70.0 g) in THF (300 ml) at -40° C. After the addition it was stirred for 11/2 hours at -40° C. then treated with water (50 ml), followed by enough 2M hydrochloric acid to make the reaction mixture just acid, this was stirred for 11/2 hours and then neutralised with sodium bicarbonate, and extracted with ether (3×300 ml). The combined ether extracts were dried and concentrated to give 2-acetyl-4-(2,2,2-trifluoroethoxy)-pyrimidine (66.8 g, 88% yield) as a brown oil; IR maxima (film): 1718 cm-1 ; 1H NMR (270 MHz): δ2.74(3H,s), 4.92(2H,q), 7.05(1H,d), 8.74(1H,d) ppm.

Workup

  1. additionAfter the addition it
  2. stirringthis was stirred for 11/2 hours
  3. extractionextracted with ether (3×300 ml)
  4. dry with materialThe combined ether extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a14c55e52a994b339553a5cb8be1b3c6
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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