2-(Methylsulfanyl)-5-[(pyridin-4-yl)methyl]pyrimidin-4(3H)-one → 2-[3-(5-Chloro-3-methylpyrid-2-ylamino)propylamino]-5-(4-pyridylmethyl)-4-pyrimidone

HRID 1906551Notes

Reaction equation

HRID 1906551 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([Cl:13])=[CH:8][N:7]=1.CS[C:16]1[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[CH:18][N:17]=1>N1C=CC=CC=1>[Cl:13][C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:16]2[NH:21][C:20](=[O:22])[C:19]([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[CH:18][N:17]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 143385852-(Methylsulfanyl)-5-[(pyridin-4-yl)methyl]pyrimidin-4(3H)-oneHCID 143973652-(3-Aminopropylamino)-5-chloro-3-methylpyridine

Product 1

HCID 202122372-[3-(5-Chloro-3-methylpyrid-2-ylamino)propylamino]-5-(4-pyridylmethyl)-4-pyrimidoneYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(3-Aminopropylamino)-5-chloro-3-methylpyridine (0.92 g) and 2-methylthio-5-(4-pyridylmethyl)-4-pyrimidone (0.90 g) were heated together under reflux in pyridine (5 ml) for 46 hr. After stripping to dryness the residue was triturated with wet ether to give a white solid. Repeated recrystallisation from isopropanol/water gave 2-[3-(5-chloro-3-methylpyrid-2-ylamino)propylamino]-5-(4-pyridylmethyl)-4-pyrimidone (0.95 g; 64%) m.p. 90°-92° C.

Workup

  1. customwas triturated with wet ether
  2. customto give a white solid
  3. customrecrystallisation from isopropanol/water

Sources & evidence

ORD record
ord-caa66a8cc75d45c9bc1483b8abd5d954
Source dataset
uspto-grants-1987_03
Patent number
US04652650

Reaction notes

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