2-(Methylthio)-4-(tributylstannyl)pyrimidine → HCID 57936290, compound

HRID 1434989Notes

Reaction equation

HRID 1434989 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]([NH2:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.[CH3:14][S:15][C:16]1[N:21]=[C:20]([Sn](CCCC)(CCCC)CCCC)[CH:19]=[CH:18][N:17]=1>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][C:10]([NH2:13])([CH3:12])[C:9]#[C:8][C:5]1[CH:4]=[CH:3][C:2]([C:18]2[CH:19]=[CH:20][N:21]=[C:16]([S:15][CH3:14])[N:17]=2)=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 27632612-(Methylthio)-4-(tributylstannyl)pyrimidine2×HCID 579361404-(5-Bromo-2-pyridinyl)-2-methyl-3-butyn-2-amine

Product 1

HCID 57936290HCID 57936290, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

3-(5-Bromo-pyridin-2-yl)-1,1-dimethyl-prop-2-ynylamine (1.05 g, 4.4 mmol), 2-methylthio-4-tri-butylstannylpyrimidine (1.83 g, 4.4 mmol) and PdCl2(PPh3)2 (154 mg, 0.22 mmol) in toluene (22 ml) were refluxed under argon for 2 hours. A second portion of 2-methylthio-4-tri-n-butylstannylpyrimidine (1.83 g, 4.4 mmol) was added and the mixture refluxed for 1 hour. The reaction mixture was filtered, evaporated and purified via chromatography on silicagel (TBME/MeOH/ammonia:97/2.7/0.3 to 95/4.5/0.5) to give the title compound as orange-brown solid, which was recrystallized form ether/hexanes. Yield: 500 mg (40%).

Workup

  1. temperaturethe mixture refluxed for 1 hour
  2. filtrationThe reaction mixture was filtered
  3. customevaporated
  4. custompurified via chromatography on silicagel (TBME/MeOH/ammonia:97/2.7/0.3 to 95/4.5/0.5)

Sources & evidence

ORD record
ord-0e09a8f821ca4d1992a5a59fefdbcc72
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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