Tri-o-tolylphosphine → HCID 14518335, compound

HRID 1723022Notes

Reaction equation

HRID 1723022 reaction equation
Br[C:2]1[CH:15]=[N:14][C:5]2[N:6]([CH3:13])[C:7](=[O:12])[N:8]([CH3:11])[C:9](=[O:10])[C:4]=2[CH:3]=1.C[Sn]([CH2:20][C:21](=[O:23])[CH3:22])(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC=CC=1>[O:23]=[C:21]([CH3:22])[CH2:20][C:2]1[CH:15]=[N:14][C:5]2[N:6]([CH3:13])[C:7](=[O:12])[N:8]([CH3:11])[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 13005248HCID 13005248, compoundHCID 14518324HCID 14518324, compound

Product 1

HCID 14518335HCID 14518335, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 167845palladium(II) acetateCatalystHCID 241BenzeneSolvent

Procedure

Treatment of 6-bromo-1,3-dimethylpyrido[2,3-d]pyrimidin-2,4-(1H,3H)-dione with trimethylstannyl acetone in the presence of a palladium catalyst such as palladium (II) acetate and a triarylphosphine such as tri-o-tolylphosphine in an anhydrous solvent such as benzene at temperatures between 50 degrees and 120 degrees C. will afford 6-(2'-oxoproply)-1,3-dimethylpyrido[2,3-d]pyrimidin-2,4-(1H,3H)-dione. Treatment of this material with N,N-dimethylformamide dimethylacetal in the presence of a catalytic amount of pyridine will afford 6-[1-N,N-dimethylamino-3'-oxobuten-2'-yl]-1,3-dimethylpyrido[2,3-d]pyrimidin-2,4-(1H,3H)-dione. Treatment of this material with cyanoacetamide in the presence of a base such as sodium hydride in a suitable solvent at temperatures between 30 degrees and 80 degrees C. will afford 6-[3'-cyano-6'-methyl-2'-oxo-1(H)pyridin-5'-yl]1,3-dimethylpyrido[2,3-d]pyrimidin-2,4-(1H,3H)-dione.

Workup

  1. customat temperatures between 50 degrees and 120 degrees C

Sources & evidence

ORD record
ord-ac411bab2521427f91322cb26a20fba2
Source dataset
uspto-grants-1989_08
Patent number
US04859672

Reaction notes

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