Water → 4,6-dichloro-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-1,3,5-triazin-2-amine
Reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[NH2:10][C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.CCN(C(C)C)C(C)C.O>C1COCC1>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:10][C@@H:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)[N:7]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of cyanuric chloride (631 mg, 3.42 mmol) in THF (2.00 mL) at 0° C. was added (S)-(+)-1-aminoindan (0.385 mL, 3.00 mmol) and DIPEA (0.596 mL, 3.42 mmol) and the mixture was stirred at 0° C. for 2 h. The reaction was then poured into H2O, extracted with DCM and the organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 0 to 20% EtOAc in hexanes to afford the title compound as a yellow solid (738 mg, 87%). LC/MS: Rt=1.99 min, ES+ 281 (FA standard).
Workup
- extractionextracted with DCM
- dry with materialthe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified via silica gel chromatography
- washeluting with a gradient of 0 to 20% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-d150df4394444341add69f363cde80ef
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481550B2
Reaction notes
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