Tetrahydrofuran → 1-(5-Fluoropyrimidin-2-yl)ethanone

HRID 415421Notes

Reaction equation

HRID 415421 reaction equation
BrC1C(NC2C=C(OC(C)C)NN=2)=NC(N[C@H:9]([C:11]2[N:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=2)[CH3:10])=NC=1.C1C[O:31]CC1.C[Mg+].[Br-]>CCOCC>[F:17][C:14]1[CH:13]=[N:12][C:11]([C:9](=[O:31])[CH3:10])=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 178418689HCID 178418689, compoundHCID 1784586625-Bromo-N2-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Product 1

HCID 509948151-(5-Fluoropyrimidin-2-yl)ethanoneYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottom-flask containing 5-fluoropyrimidine-2-carbonitrile (Method 6, 1.50 g, 12.19 mmol) was charged with anhydrous THF (30 ml) under N2. The solution was cooled to 0° C., and a solution of MeMgBr (4.90 ml of a 3.0 M solution in ether, 14.62 mmol) was added dropwise. After 2 hours at 0° C., the reaction mixture was quenched with ice water and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness to give the title compound as an oil (0.778 g, yield 46%). GC-MS, 140 (M); 1H NMR (CDCl3) δ 8.65 (s, 2H), 2.65 (s, 2H).

Workup

  1. customthe reaction mixture was quenched with ice water
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-addee038fbd64671bc67b30a54bdb452
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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