4-Amino-6-methoxypyrimidine → 4-Isothiocyanato-6-methoxypyrimidine

HRID 1875882Notes

Reaction equation

HRID 1875882 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

HCID 7357314-Amino-6-methoxypyrimidineHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridone

Product 1

HCID 574765514-Isothiocyanato-6-methoxypyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (1H, d, J=5.79 Hz), 6.95 (1H, d, J=5.79 Hz), 3.92 (3H, s). MS (LC/MS) R.T.=3.15; [M+H]+=168.1.

Sources & evidence

ORD record
ord-d3f1ed81342f49449eb842f29c271fd1
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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