Triphenylphosphine → N-(3-methyl-5-(1-(3-methylbut-3-en-2-yl)-1H-pyrazol-4-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 595170Notes

Reaction equation

HRID 595170 reaction equation
N(/C(OC(C)(C)C)=O)=N\C(OC(C)(C)C)=O.[CH3:17][C:18](=[CH2:22])[CH:19](O)[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:42][C:43]1[CH:44]=[C:45]([NH:54][C:55]2[N:60]=[C:59]([C:61]([F:64])([F:63])[F:62])[CH:58]=[CH:57][N:56]=2)[CH:46]=[C:47]([C:49]2[CH:50]=[N:51][NH:52][CH:53]=2)[CH:48]=1>C1COCC1>[CH3:42][C:43]1[CH:44]=[C:45]([NH:54][C:55]2[N:60]=[C:59]([C:61]([F:62])([F:64])[F:63])[CH:58]=[CH:57][N:56]=2)[CH:46]=[C:47]([C:49]2[CH:50]=[N:51][N:52]([CH:19]([C:18]([CH3:22])=[CH2:17])[CH3:20])[CH:53]=2)[CH:48]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 663293-Methyl-3-buten-2-olHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 118208677N-(3-methyl-5-(1H-pyrazol-4-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Product 1

HCID 118208706N-(3-methyl-5-(1-(3-methylbut-3-en-2-yl)-1H-pyrazol-4-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(E)-di-tert-butyl diazene-1,2-dicarboxylate (321 mg, 1.39 mmol) was added slowly to a 0° C. well stirred solution of 3-methylbut-3-en-2-ol (100 mg, 1.16 mmol), triphenylphosphine (365 mg, 1.39 mmol) and N-(3-methyl-5-(1H-pyrazol-4-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine (371 mg, 1.16 mmol) in THF (3.5 mL). The reaction was stirred for 10 min and allowed to warm to RT for 18 hours. The reaction was quenched into aqueous potassium hydrogen sulfate (5%, 20 mL) and product extracted with ethyl acetate (2×20 mL). The organic extracts were combined dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10-50% ethyl acetate/hexanes) to afford N-(3-methyl-5-(1-(3-methylbut-3-en-2-yl)-1H-pyrazol-4-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine MS ESI calcd. for C20H21F3N5 [M+H]+ 388. found 388.

Workup

  1. customThe reaction was quenched into aqueous potassium hydrogen sulfate (5%, 20 mL) and product
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe organic extracts were combined dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica (10-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f78d859d895d4f16b7a706cf92207425
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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