Hydrochloric Acid → HCID 68686065, compound

HRID 1441328Notes

Reaction equation

HRID 1441328 reaction equation
[N:1]([CH:4]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH:26]([CH3:28])[CH3:27])[C:24]([CH3:29])=[N:23][CH:22]=4)[C:18]([F:30])=[CH:17][N:16]=3)=[CH:10][CH:9]=2)[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.Cl>C1COCC1>[NH2:1][CH:4]1[CH2:5][N:6]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH:26]([CH3:27])[CH3:28])[C:24]([CH3:29])=[N:23][CH:22]=4)[C:18]([F:30])=[CH:17][N:16]=3)=[CH:12][CH:13]=2)[CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 86613525HCID 86613525, compound

Product 1

HCID 68686065HCID 68686065, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution N-[4-(3-azidoazetidin-1-yl)phenyl]-5-fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-amine (Example 139; 382 mg, 938 mM) in THF (10 ml), triphenylphosphine (260 mg, 0.984 mM) was added. The reaction was stirred at room temperature under nitrogen for 24 hours. Water (2.0 ml) was then added and the mixture stirred and heated at 65° C. for 3 hours. Hydrochloric acid (1M, 1.5 ml) was added and the THF removed in vacuo. More water was then added and the solution extracted with EtOAc. Sodium hydroxide (1M, 1.5 ml) was added to the water layer and the solution was extracted with EtOAc. The organic layers were combined, dried with anhydrous sodium sulphate, filtered and evaporated to give the title compound as a yellow foam (324 mg, 91%). NMR (DMSO-d6+d4-acetic acid) 1.38 (d, 6H), 2.5 (s, 3H), 3.73 (m, 2H), 4.05 (m, 3H), 5.43 (m, 1H), 6.45 (d, 2H), 7.33 (s, 1H), 7.4 (d, 2H), 8.4 (d, 1H); m/z 382.

Workup

  1. stirringthe mixture stirred
  2. temperatureheated at 65° C. for 3 hours
  3. customthe THF removed in vacuo
  4. additionMore water was then added
  5. extractionthe solution extracted with EtOAc
  6. additionSodium hydroxide (1M, 1.5 ml) was added to the water layer
  7. extractionthe solution was extracted with EtOAc
  8. dry with materialdried with anhydrous sodium sulphate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-ba24d7290cac46b98115ea0d1fbd7bc7
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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