tert-Butanol → HCID 11199740, compound
Reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=3[CH:9]=[C:8](C(O)=O)[C:7]2=[O:21])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:24]([CH2:27]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.[C:46]([OH:50])([CH3:49])([CH3:48])[CH3:47]>>[C:46]([O:50][C:27](=[O:36])[NH:24][C:8]1[C:7](=[O:21])[N:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:11]2[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=2[CH:9]=1)([CH3:49])([CH3:48])[CH3:47]Participants
Conditions
- Temperature
- 75 °C
Procedure
To anhydrous t-butanol (30 ml) was added 8-cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid (2.48 g, 8.02 mmol), triethylamine (0.974 g, 9.63 mmol) and over 5 minutes, diphenylphosphorylazide (2.65 g, 9.63 mmol) with stirring. This mixture was heated at 75° C. for 18 hours. The mixture was filtered and the solid was washed with ethyl acetate. The washings were concentrated to an oil enriched in the desired product. The oil was triturated with hexane/diethyl ether and the washings were filtered through silica gel and celite. The filtrate was concentrated in vacuo yielding (8-cyclopentyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-carbamic acid tert-butyl ester as a crystalline solid (1.37 g, 45%). MS (APCI): M++1: Calc'd, 377.16. Found 377.2.
Workup
- filtrationThe mixture was filtered
- washthe solid was washed with ethyl acetate
- concentrationThe washings were concentrated to an oil
- customThe oil was triturated with hexane/diethyl ether
- filtrationthe washings were filtered through silica gel and celite
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-5825061a814343128f9d476a4884d344
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456168B2
Reaction notes
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