Triethylamine → (1S,2R,4R)-4-[(6-Chloropyrimidin-4-yl)amino]-2-(hydroxymethyl)cyclopentanol
Reaction equation
[NH2:1][C@H:2]1[CH2:6][C@H:5]([OH:7])[C@@H:4]([CH2:8][OH:9])[CH2:3]1.[Cl:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.CCN(CC)CC>C(O)(C)C>[Cl:10][C:11]1[N:12]=[CH:13][N:14]=[C:15]([NH:1][C@H:2]2[CH2:6][C@H:5]([OH:7])[C@@H:4]([CH2:8][OH:9])[CH2:3]2)[CH:16]=1Participants
5
Conditions
- Temperature
- 90 °C
Procedure
To a neat mixture of (1S,2R,4R)-4-amino-2-(hydroxymethyl)cyclopentanol (3.00 g, 22.9 mmol) and 4,6-dichloropyrimidine (3.70 g, 24.8 mmol) was added isopropyl alcohol (30.0 mL) and Et3N (8.00 mL, 57.4 mmol) and the resulting mixture was heated to 90° C. for 1 h. The mixture was then cooled to 23° C., filtered and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 5 to 7% MeOH in DCM, and the compound was recrystallized from EtOAc to afford the title compound as a white solid (3.30 g, 59%). LC/MS: Rt=0.84 min, ES+ 244 (AA standard).
Workup
- temperatureThe mixture was then cooled to 23° C.
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified via silica gel chromatography
- washeluting with a gradient of 5 to 7% MeOH in DCM
- customthe compound was recrystallized from EtOAc
Sources & evidence
- ORD record
- ord-587d5b39b2e2439ea08500b8c27da3cc
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481550B2
Reaction notes
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