Triphenylphosphine → 4-[4-(Benzyloxy)butoxy]-6-(trifluoromethyl)pyrimidine

HRID 384455

Reaction equation

HRID 384455 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:14][C:15]([F:24])([F:23])[C:16]1[N:21]=[CH:20][N:19]=[C:18](O)[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:18]1[CH:17]=[C:16]([C:15]([F:24])([F:23])[F:14])[N:21]=[CH:20][N:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5622124-Benzyloxy-1-butanolHCID 178516143HCID 178516143, compound

Product 1

HCID 595272614-[4-(Benzyloxy)butoxy]-6-(trifluoromethyl)pyrimidineYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(benzyloxy)butan-1-ol (3.00 g), 6-(trifluoromethyl)pyrimidin-4-ol (3.00 g), and triphenylphosphine (5.25 g) in THF (30 mL) was added diisopropyl azodicarboxylate (4.05 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to obtain 4-[4-(benzyloxy)butoxy]-6-(trifluoromethyl)pyrimidine (2.83 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-456c051eee1c446ea8710e55bc88f3cb
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Linked notes

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