Diisopropylethylamine → (S)-methyl 3-((6-carbamoyl-2-chloropyrimidin-4-yl)amino)-2-hydroxypropanoate
Reaction equation
Cl.[NH2:2][CH2:3][C@H:4]([OH:9])[C:5]([O:7][CH3:8])=[O:6].[Cl:10][C:11]1[N:16]=[C:15]([C:17]([NH2:19])=[O:18])[CH:14]=[C:13](Cl)[N:12]=1.CCN(C(C)C)C(C)C>C(#N)C>[C:17]([C:15]1[N:16]=[C:11]([Cl:10])[N:12]=[C:13]([NH:2][CH2:3][C@H:4]([OH:9])[C:5]([O:7][CH3:8])=[O:6])[CH:14]=1)(=[O:18])[NH2:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a mixture of the (S)-methyl 3-amino-2-hydroxypropanoate hydrochloride (0.333 g, 2.14 mmol) in acetonitrile (10 mL) was added 2,6-dichloropyrimidine-4-carboxamide (0.385 g, 2.01 mmol) and iPr2NEt (0.77 mL, 4.4 mmol). The mixture was heated at 50° C. overnight then cooled. The precipitated solid was filtered off, rinsed once with 2 mL acetonitrile, and air-dried to give (S)-methyl 3-((6-carbamoyl-2-chloropyrimidin-4-yl)amino)-2-hydroxypropanoate as a pale peach-colored powder (0.421 g, 1.53 mmol, 76% yield). LC/MS: m/z=275.1 [M+H]+.
Workup
- temperaturethen cooled
- filtrationThe precipitated solid was filtered off
- washrinsed once with 2 mL acetonitrile
- customair-dried
Sources & evidence
- ORD record
- ord-4167419ebf4b4a54ba890ca2ca764cc4
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163008B2
Reaction notes
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