HCID 44815809, compound → HCID 44815810, compound

HRID 1187447Notes

Reaction equation

HRID 1187447 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:21]2[CH:22]=[N:23][C:24]([C:27](=[O:29])[CH3:28])=[N:25][CH:26]=2)=[N:6][CH:7]=1.[CH3:30][Mg]Br>C1COCC1.[NH4+].[Cl-]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:21]2[CH:22]=[N:23][C:24]([C:27]([OH:29])([CH3:30])[CH3:28])=[N:25][CH:26]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 44815809HCID 44815809, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 44815810HCID 44815810, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 1-(5-{5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}pyrimidin-2-yl)ethanone (Example 73) (12 mg, 0.03 mmol) in THF (5 mL) was treated with methylmagnesium bromide (0.09 mL, 0.3 mmol, 3.0 M in THF) at rt. Upon completion of the reaction as judged by TLC analysis, the solution was diluted with saturated aq NH4Cl solution and extracted with EtOAc. The organic layer was removed, dried over MgSO4, filtered and concentrated giving rise to an oil. The oil was purified on silica gel to afford the title compound (6.3 mg). LC/MS: m/e 443.0 (M+H)+. 1H NMR (500 MHz, Acetone-d6): δ 1.54 (s, 6H), 4.56 (s, 1H), 7.39 (m, 2H), 7.47 (d, J=8.5 Hz, 1H), 7.82 (m, 1H), 8.25 (m, 2H), 8.45 (d, J=2.5 Hz, 1H), 9.39 (s, 2H).

Workup

  1. customUpon completion of the reaction
  2. extractionextracted with EtOAc
  3. customThe organic layer was removed
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customgiving rise to an oil
  8. customThe oil was purified on silica gel

Sources & evidence

ORD record
ord-43350a843580478f8b0ad9b84e32dfe5
Source dataset
uspto-grants-2014_03
Patent number
US08673941B2

Reaction notes

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