2-Butanamine, 2-methyl- → HCID 70982239, compound

HRID 2280778Notes

Reaction equation

HRID 2280778 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[CH3:12][C:13]([NH2:17])([CH2:15][CH3:16])[CH3:14].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:11][S:10][C:4]1[N:3]=[C:2]([NH:17][C:13]([CH2:15][CH3:16])([CH3:14])[CH3:12])[C:7]([C:8]#[N:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 689862-Butanamine, 2-methyl-HCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Product 1

HCID 70982239HCID 70982239, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-Chloro-2-(methylthio)pyrimidine-5-carbonitrile (500 mg, 2.69 mmol) was dissolved in DMF (5 mL), 2-methylbutan-2-amine (0.378 mL, 3.24 mmol) and DIEA (1.411 mL, 8.08 mmol) were added and the reaction was heated at 70° C. overnight. LCMS showed the desired product mass as the dominant peak and no starting material remaining. The reaction was removed from heat and partitioned between ethyl acetate and water. The organic layer was washed once with brine before drying over magnesium sulfate, filtering, and condensing. The crude material was purified by silica gel chromatography (0-80% ethyl acetate in hexane over 1650 mL; 40 mL/min). Product fractions were combined, evaporated, and dried under high vacuum to afford 2-(methylthio)-4-(tert-pentylamino)pyrimidine-5-carbonitrile (359 mg, 1.519 mmol, 56.4% yield) as a white solid; MS (ESI) m/z 236.9 [M+1]+

Sources & evidence

ORD record
ord-cb9195c3f7924eeea03f1e82ebafcac5
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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