1-Phenethylamine, (+)- → 2-[((R)-1-phenyl-ethylamino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one
Reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[CH2:12][O:11][CH2:10][CH2:9][C:7]=2[N:8]=1.[C:14]1([C@H:20]([NH2:22])[CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:14]1([C@H:20]([NH:22][CH2:2][C:3]2[NH:4][C:5](=[O:13])[C:6]3[CH2:12][O:11][CH2:10][CH2:9][C:7]=3[N:8]=2)[CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
Conditions
- Temperature
- 65 °C
Procedure
To 2-chloromethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (50 mg, 0.249 mmol) in ethanol (2 mL) was added (R)-1-phenyl-ethylamine (66 mg, 0.545 mmol, 2 eq) and the solution was heated at 65° C. for 15 h. The cooled solution was concentrated under vacuum and the resulting oil was taken up in methanol, added to a strong cation exchange (SCX) column and washed with methanol (50 mL). The product was eluted with 1 N ammonia in methanol (50 mL) and concentrated under vacuum. The crude product was absorbed onto Silica Gel (500 mg), added to a Biotage SNAP-10 g column and eluted with 1% to 10% methanol in dichlormethane over 12 column volumes to give: 2-[((R)-1-phenyl-ethylamino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (20 mg, 28% yield). Exact mass calculated for C16H19N3O2 285.15. found 286.5 (ESI, M+H).
Workup
- concentrationThe cooled solution was concentrated under vacuum
- additionadded to a strong cation exchange (SCX) column
- washwashed with methanol (50 mL)
- washThe product was eluted with 1 N ammonia in methanol (50 mL)
- concentrationconcentrated under vacuum
- customThe crude product was absorbed onto Silica Gel (500 mg)
- additionadded to a Biotage SNAP-10 g column
- washeluted with 1% to 10% methanol in dichlormethane over 12 column volumes
- customto give
Sources & evidence
- ORD record
- ord-8aef7a6d162b43de8abe7074b4313927
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181266B2
Reaction notes
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