3-Aminopyridine → 2-Isopropyl-5-(pyridin-3-ylamino)-pyrimidine-4-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

HRID 2368349Notes

Reaction equation

HRID 2368349 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[O:10])[NH:8][CH3:9])=[C:5]([NH:11][C:12]([C:14]2[C:19](Br)=[CH:18][N:17]=[C:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[O:13])[CH:4]=[N:3]1.[NH2:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH3:1][N:2]1[C:6]([C:7](=[O:10])[NH:8][CH3:9])=[C:5]([NH:11][C:12]([C:14]2[C:19]([NH:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:18][N:17]=[C:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)=[O:13])[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866601955-Bromo-2-isopropyl-pyrimidine-4-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

Product 1

HCID 547609462-Isopropyl-5-(pyridin-3-ylamino)-pyrimidine-4-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-2-isopropyl-pyrimidine-4-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide (40 mg, 105 μmol), 3-aminopyridine (15 mg, 157 μmol) and potassium phosphate tribasic (31 mg, 147 μmol) in toluene (1 ml) was treated with tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (10.9 mg, 10.5 μmol) and xantphos (20 mg, 34.6 μmol) were added and the reaction mixture was stirred at 120° C. for 16 h. The reaction was cooled to r.t., filtrated and the product was obtained after purification by preparative HPLC using an acetonitrile/water gradient as yellow solid (10 mg, 25%).

Workup

  1. additionwere added
  2. temperatureThe reaction was cooled to r.t.
  3. filtrationfiltrated
  4. customthe product was obtained
  5. customafter purification by preparative HPLC

Sources & evidence

ORD record
ord-9aa2ea81ee5a4e92be93dd2db7784b83
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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