Allyl Alcohol → (4,6-Dichloro-2-methylsulfanylpyrimidin-5-yl)carbamic acid allyl ester
Reaction equation
[Cl:1][C:2]1[C:7](C(O)=O)=[C:6]([Cl:11])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:21])C=CC=CC=1.C([N:33]([CH2:36]C)CC)C.[CH2:38]([OH:41])[CH:39]=[CH2:40]>O1CCOCC1.CCOC(C)=O>[CH2:38]([O:41][C:36](=[O:21])[NH:33][C:7]1[C:2]([Cl:1])=[N:3][C:4]([S:12][CH3:13])=[N:5][C:6]=1[Cl:11])[CH:39]=[CH2:40]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 4,6-dichloro-2-methylsulfanylpyrimidine-5-carboxylic acid (5.5 mmol) in dioxane (10 mL) are added diphenyl phosphoryl azide (6.6 mmol), triethylamine (6.6 mmol) and allyl alcohol (11 mmol) at room temperature under N2 atmosphere. After stirring at 100° C. for 1 h, the reaction mixture is cooled to room temperature and diluted with AcOEt. The organic layer is washed twice with H2O and evaporated in vacuo. The resulting residue is purified by silica gel column chromatography to give (4,6-dichloro-2-methylsulfanylpyrimidin-5-yl)carbamic acid allyl ester.
Workup
- temperaturethe reaction mixture is cooled to room temperature
- washThe organic layer is washed twice with H2O
- customevaporated in vacuo
- customThe resulting residue is purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-cd432a50e39043cab54dcf38b5dc74d1
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07704996B2
Reaction notes
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