Nitrogen → HCID 178437727, compound

HRID 1530824Notes

Reaction equation

HRID 1530824 reaction equation
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[CH:17]=[C:16]([CH2:18][CH3:19])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].N#N.[F:22]F>FC(F)(F)C(O)=O>[C:1]([C@@H:5]1[CH2:6][CH2:7][C@H:8]([NH:11][C:12]2[C:17]([F:22])=[C:16]([CH2:18][CH3:19])[N:15]=[CH:14][N:13]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 947NitrogenHCID 24524FluorineHCID 178436813HCID 178436813, compound

Product 1

HCID 178437727HCID 178437727, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2.62 g of 4-(cis-4-tert-butylcyclohexylamino)-6-ethyl pyrimidine in 40 ml of trifluoroacetic acid was charged into a reactor for direct fluorination. A stream of a mixture of F2/N2 (1:10 by volume) was passed through the mixture at 15° C. After 0.015 mol of fluorine was passed through, the reaction was flushed with nitrogen in order to remove unconsumed fluorine. The solvent was removed in vacuo and the residue was treated with 50 ml of 2N sodium hydroxide, extracted with diethyl ether, washed with water and dried over MgSO4. After ether evaporation, the product was isolated in 41% yield by column chromatography, eluting with a mixture hexane/ethyl acetate 2:1.

Workup

  1. customwas passed through the mixture at 15° C
  2. customwas flushed with nitrogen in order
  3. customto remove unconsumed fluorine
  4. customThe solvent was removed in vacuo
  5. additionthe residue was treated with 50 ml of 2N sodium hydroxide
  6. extractionextracted with diethyl ether
  7. washwashed with water
  8. dry with materialdried over MgSO4
  9. customAfter ether evaporation
  10. customthe product was isolated in 41% yield by column chromatography
  11. washeluting with a mixture hexane/ethyl acetate 2:1

Sources & evidence

ORD record
ord-812a6f581995466f968617525fa39553
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

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