2-Methylthio-5-cyclohexylmethylpyrimid-4-one → 2-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]-5-cyclohexylmethyl pyrimid-4-one

HRID 464371Notes

Reaction equation

HRID 464371 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:7][CH2:8][CH3:9].CS[C:18]1[NH:23][C:22](=[O:24])[C:21]([CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][N:19]=1>N1C=CC=CC=1>[CH2:7]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:18]1[NH:23][C:22](=[O:24])[C:21]([CH2:25][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[CH:20][N:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 127838372-Methylthio-5-cyclohexylmethylpyrimid-4-oneHCID 201866172-[N-(4-aminobutyl)-N-propylamino]pyridine

Product 1

HCID 202628992-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]-5-cyclohexylmethyl pyrimid-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[N-(4-aminobutyl)-N-propylamino]pyridine (1.17 g) and 2-methylthio-5-cyclohexylmethylpyrimid-4-one (0.9 g) were heated together under reflux in pyridine (2.5 ml) for 28 hrs. After stripping, the residue was chromatographed (silica gel, dichloromethane/methanol 40:1) crystallized from ethanol/water and recrystallized from acetone/water to give 2-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]-5-cyclohexylmethyl pyrimid-4-one 1.4 H2O, 0.62 g (38%) m.p. 62°-64° C.

Workup

  1. customthe residue was chromatographed (silica gel, dichloromethane/methanol 40:1)
  2. customcrystallized from ethanol/water
  3. customrecrystallized from acetone/water

Sources & evidence

ORD record
ord-5d51a08f74b3449090f1c81e1945b6b3
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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