Potassium Carbonate → 8-t-Butyl-2-(4,6-dimethoxy pyrimid-2-ylaminomethyl)-1,4-dioxaspiro(4,5)decane
Reaction equation
[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH:11]([CH2:13][NH2:14])[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21](S(C)(=O)=O)[N:20]=1.C(=O)([O-])[O-].[K+].[K+]>>[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH:11]([CH2:13][NH:14][C:21]3[N:22]=[C:23]([O:25][CH3:26])[CH:24]=[C:19]([O:18][CH3:17])[N:20]=3)[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
8-t-butyl-2-aminomethyl-1,4-dioxaspiro(4,5)decane (3.3 g, 14.5 mmol), 4,6-dimethoxy-2-methylsulfonyl-pyrimidine (3.16 g, 14.5 mmol) and potassium carbonate (2.76 g, 20 mmol) were heated to 160° C. for 1 hour. The reaction mixture was then extracted with toluene and the concentrated extracts purified by flash chromatography using a 3:1 mixture of toluene and ethylacetate. 3.5 g of a faint yellow oil was obtained which crystallised on standing. NMR analysis indicated the product being a mixture of diastereoisomers. M.p.: 76°-106° C.
Workup
- extractionThe reaction mixture was then extracted with toluene
- customthe concentrated extracts purified by flash chromatography
- additiona 3:1 mixture of toluene and ethylacetate
Sources & evidence
- ORD record
- ord-bf70ebbb219e42a3a411d90380f15213
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616708
Reaction notes
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