Potassium Phosphate, Tribasic → HCID 86649624, compound

HRID 1897941Notes

Reaction equation

HRID 1897941 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][Si:11]([CH3:23])([CH3:22])[CH2:12][CH2:13][O:14][CH2:15][N:16]1[CH:20]=[CH:19][C:18]([NH2:21])=[N:17]1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:21][C:18]2[CH:19]=[CH:20][N:16]([CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:23])([CH3:22])[CH3:10])[N:17]=2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 794712,4-Dichloro-6-methylpyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57562604HCID 57562604, compound

Product 1

HCID 86649624HCID 86649624, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 405.9 mg of 2,4-dichloro-6-methylpyrimidine, 585.5 mg of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-amine (WO2006/046734, page 132, Reference 2), 231.9 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 208.6 mg of tris(dibenzylideneacetone)dipalladium(0)-chloroform complex, 751.2 mg of potassium phosphate and 20 ml of 1,4-dioxane was stirred at 80° C. overnight, followed by cooling to room temperature. The reaction mixture was diluted with ethyl acetate. An insoluble matter was filtered off using Celite, and washed with ethyl acetate. The filtrate was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1−2/3) to give the title compound.

Workup

  1. temperatureby cooling to room temperature
  2. filtrationAn insoluble matter was filtered off
  3. washwashed with ethyl acetate
  4. washThe filtrate was washed with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=10/1−2/3)

Sources & evidence

ORD record
ord-917940259b6d4306b7f7db337285632d
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

Loading…