Ammonia → 1-(4-Methyl-1-(6-methylpyrimidin-4-yl)piperidin-4-yl)thiourea

HRID 451548Notes

Reaction equation

HRID 451548 reaction equation
[N:1]([C:4]1([CH3:17])[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12][N:11]=2)[CH2:6][CH2:5]1)=[C:2]=[S:3].[NH3:18]>>[CH3:17][C:4]1([NH:1][C:2]([NH2:18])=[S:3])[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12][N:11]=2)[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 583978594-(4-Isothiocyanato-4-methylpiperidin-1-yl)-6-methylpyrimidine

Product 1

HCID 583978821-(4-Methyl-1-(6-methylpyrimidin-4-yl)piperidin-4-yl)thioureaYield 853.2%

Conditions

Temperature
50 °C

Procedure

A solution of 4-(4-isothiocyanato-4-methylpiperidin-1-yl)-6-methylpyrimidine (1.18 g, 0.53 mmol) in ammonia (7 M in MeOH, 13.6 mL, 95.0 mmol) was stirred in a sealed tube at room temperature for 3 h and then heated at 50° C. for 18 h. After cooling to room temperature the mixture was evaporated. Purification by chromatography (silica gel, 50 g, 0 to 20% methanol in dichloromethane) afforded the title compound (1.2 g, 100%) as a white foam.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customwas evaporated
  3. customPurification by chromatography (silica gel, 50 g, 0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e8ff04aaafd74eb195ae0ef207260f27
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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