Diisopropylamine → HCID 178428353, compound

HRID 474014Notes

Reaction equation

HRID 474014 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[N:3]=1.C(NC(C)C)(C)C.[CH3:21][C:22]1[CH:26]=[C:25]([NH2:27])[NH:24][N:23]=1>C1COCC1.C(OCC)(=O)C.O>[Cl:9][C:6]1[N:5]=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[N:3]=[C:2]([NH:27][C:25]2[NH:24][N:23]=[C:22]([CH3:21])[CH:26]=2)[C:7]=1[F:8]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 866162574,6-Dichloro-5-fluoro-2-methanesulfonylpyrimidineHCID 178418690HCID 178418690, compound

Product 1

HCID 178428353HCID 178428353, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,6-dichloro-5-fluoro-2-(methylsulfonyl)pyrimidine in THF (25 ml) was added diisopropylamine (1.32 g, 10.20 mmol, 1.82 ml) and 3-methyl-1H-pyrazol-5-amine (1.04 g, 10.71 mmol) and the mixture stirred at room temperature for 30 mins. The reaction was diluted with ethyl acetate (100 ml) and water (100 ml), the organic layer was washed with brine (50 ml), dried (Na2SO4), and partially concentrated until a solid started to precipitate. The suspension was cooled in an ice bath for 1 hr and filtered to give the title compound as a pale yellow solid. A second crop was obtained by leaving the filtrate to stand overnight (total 1.55 g, 50%). 1H NMR (DMSO, 400 MHz) 2.26 (3H, s), 3.32 (3H, s), 6.48 (1H, s), 11.03 (1H, s), 12.35 (1H, s) ES+306.

Workup

  1. washthe organic layer was washed with brine (50 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationpartially concentrated until a solid
  4. customto precipitate
  5. temperatureThe suspension was cooled in an ice bath for 1 hr
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2b4916e28677498899dba0e3f0ada9f3
Source dataset
uspto-grants-2014_01
Patent number
US08637511B2

Reaction notes

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