Cyanamide → HCID 178437136, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([S:10][CH3:11])[CH3:9])=[CH:4][N:3]=1.[N:12]#[C:13][NH2:14].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]([S:10]([CH3:11])=[N:14][C:13]#[N:12])[CH3:9])=[CH:6][N:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-chloro-5-[1-(methylthio)ethyl]pyrimidine (0.49 g, 2.61 mmol) and cyanamide (120 mg, 2.86 mmol) in 20 mL of CH2Cl2 was cooled to 0° C. and treated with iodobenzene diacetate (860 mg, 2.59 mmol). The mixture was allowed to warm to room temperature over an hour, the solvent was removed under reduced pressure and the residue was partitioned between hexanes and acetonitrile. The acetonitrile was removed under reduced pressure and the residue was further purified by flash column chromatography on silica gel using a 50% mixture of acetone and petroleum ether as the eluant. The solvents were removed under reduced pressure to yield 0.44 g (74%) of (1E)-[1-(2-chloropyrimidin-5-yl)ethyl](methyl)-λ4-sulfanylidenecyanamide (C) as a pale orange syrup. This material was a 2:1 mixture of diastereomers. The physical properties of the major diastereomer were: 1H NMR (CDCl3) δ 8.68 (s, 2H), 4.38 (q, J=8.3 Hz, 1H), 2.68 (s, 3H), 1.92 (d, J=8.3 Hz, 3H); LC-MS (ESI) m/z 229 (M+H).
Workup
- customthe solvent was removed under reduced pressure
- customthe residue was partitioned between hexanes and acetonitrile
- customThe acetonitrile was removed under reduced pressure
- customthe residue was further purified by flash column chromatography on silica gel using a 50% mixture of acetone and petroleum ether as the eluant
- customThe solvents were removed under reduced pressure
Sources & evidence
- ORD record
- ord-37ea5129dd8c464e9f1a7eceb0e1645f
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324209B2
Reaction notes
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