1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-Isothiocyanato-6-(methoxymethyl)pyrimidine

HRID 1875911

Reaction equation

HRID 1875911 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH3:17][O:18][CH2:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=1>ClCCl>[N:26]([C:22]1[CH:21]=[C:20]([CH2:19][O:18][CH3:17])[N:25]=[CH:24][N:23]=1)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 211376446-(Methoxymethyl)-4-pyrimidinamine

Product 1

HCID 574765584-Isothiocyanato-6-(methoxymethyl)pyrimidineYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a bright orange solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.84 g, 3.59 mmol) was in dichloromethane at ambient temperature was added 6-(methoxymethyl)pyrimidin-4-amine (0.5 g, 3.59 mmol). The orange solution was stirred at ambient temperature for 18 h. The solution was purified by column chromatography (0-40% ethyl acetate/hexanes) to afford 4-isothiocyanato-6-(methoxymethyl)pyrimidine (0.32 g, 1.77 mmol, 49% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.91 (1H, d, J=1.26 Hz), 7.19 (1H, d, J=1.01 Hz), 4.52 (2H, s), 3.49 (3H, s). MS (LC/MS) R.T.=1.39; [M+H]+=182.10.

Workup

  1. customThe solution was purified by column chromatography (0-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-583f225c27bf46e997f710183d6507e1
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Linked notes

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