1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-(4-Isothiocyanato-4-methylpiperidin-1-yl)-6-methylpyrimidine

HRID 451547Notes

Reaction equation

HRID 451547 reaction equation
[CH3:1][C:2]1([NH2:15])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[C:16](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:17]>ClCCl>[N:15]([C:2]1([CH3:1])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10][N:9]=2)[CH2:4][CH2:3]1)=[C:16]=[S:17]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 583980494-Methyl-1-(6-methylpyrimidin-4-yl)piperidin-4-amine

Product 1

HCID 583978594-(4-Isothiocyanato-4-methylpiperidin-1-yl)-6-methylpyrimidineYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-1-(6-methylpyrimidin-4-yl)piperidin-4-amine (1.09 g, 5.28 mmol) in dichloromethane (17.2 mL) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (1.84 g, 7.92 mmol) and the reaction mixture was stirred at room temperature for 16 hours. After cooling to room temperature the mixture was evaporated. Purification by chromatography (silica gel, 3×70 g, 50 to 100% ethyl acetate in heptane) afforded the title compound (1.2 g, 91%) as a light yellow solid. MS ISP (m/e): 249.1 [(M+H)+].

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customwas evaporated
  3. customPurification by chromatography (silica gel, 3×70 g, 50 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-7a4dddee9bb0459ba13a52b5196930aa
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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