4-Amino-6-methoxypyrimidine → 4-Isothiocyanato-6-methoxypyrimidine
Reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH3:17][O:18][C:19]1[N:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=1>ClCCl>[N:25]([C:21]1[CH:20]=[C:19]([O:18][CH3:17])[N:24]=[CH:23][N:22]=1)=[C:1]=[S:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a bright orange solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (1.86 g, 7.99 mmol) in dichloromethane at room temperature was added 6-methoxypyrimidin-4-amine (1 g, 8 mmol). The orange solution was stirred at room temperature for 18 hours. The LC/MS showed the desired product as one of the major peaks. The deep orange solution was concentrated and the remaining residue was filtered. The filtrate was purified by silica gel chromatography (10-50% ethyl acetate/hexanes) to afford 4-isothiocyanato-6-methoxypyrimidine (0.72 g, 4.3 mmol, 54% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.49 (1 H, d, J=5.79 Hz), 6.95 (1 H, d, J=5.79 Hz), 3.92 (3 H, s). MS (LC/MS) R.T.=3.15; [M+H]+=168.1.
Sources & evidence
- ORD record
- ord-67d6ec4af63e40298322d53bc9da8da2
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863291B2
Reaction notes
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