Water → 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH2:9])=[CH:4][N:3]=1.Cl.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH:12]1[C:17](O)=[O:18].C(N(CC)C(C)C)(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:9][C:17](=[O:18])[CH:12]3[CH2:13][O:14][CH2:15][CH2:16][N:11]3[C:6]=2[N:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2,4-Dichloropyrimidin-5-amine (25 g, 152 mmol) and morpholine-3-carboxylic acid hydrochloride (28.1 g, 168 mmol) were dissolved in DMSO (200 mL) to give a yellow suspension. To the suspension was added N,N-diisopropylethylamine (106 mL, 610 mmol) and the mixture was heated to 100° C. for 18 hours. The mixture was cooled to room temperature and poured into ice. Water was added until the total volume was 1 L. The resulting beige suspension was stirred overnight before the solid was collected on a fritted-glass funnel of medium porosity. The solid was washed with water (3×) and then dried under a stream of nitrogen overnight to afford the title compound as a light yellow solid that was used without further purification (18.6 g, 51%). ESI-MS m/z [M+H]+ calc'd for C9H9ClN4O2, 241.04. found 241.1.
Workup
- customto give a yellow suspension
- temperatureThe mixture was cooled to room temperature
- additionpoured into ice
- customwas collected on a fritted-glass funnel of medium porosity
- washThe solid was washed with water (3×)
- customdried under a stream of nitrogen overnight
Sources & evidence
- ORD record
- ord-6a4e4d5d5ff0483a82a3744bf1730a2c
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08791107B2
Reaction notes
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