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Trimethylsilyl triflate → 9-((4s,5s)-4-Azido-5-((tert-butyldimethylsilyloxy)methyl)tetrahydrofuran-2-yl)-6-chloro-9h-purin-2-amine

HRID 2408267
Notes
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Reaction equation

HRID 2408267 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[O:7][C@@H:6](N2C=CC(=O)NC2=O)[CH2:5]1)=[N+:2]=[N-:3].[NH2:26][C:27]1[N:35]=[C:34]2[C:30]([NH:31][CH:32]=[N:33]2)=[C:29]([Cl:36])[N:28]=1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13])[O:7][CH:6]([N:33]2[CH:32]=[N:31][C:30]3[C:34]2=[N:35][C:27]([NH2:26])=[N:28][C:29]=3[Cl:36])[CH2:5]1)=[N+:2]=[N-:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 53603492-Amino-6-chloropurineHCID 107851963'-Azido-5'-O-tert-butyldimethylsilyl-2',3'-dideoxyuridine

Product 1

HCID 913019059-((4s,5s)-4-Azido-5-((tert-butyldimethylsilyloxy)methyl)tetrahydrofuran-2-yl)-6-chloro-9h-purin-2-amine

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 1-((2R,4S,5S)-4-azido-5-((tert-butyldimethylsilyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H, 3H)-dione, 75 (TBS protected AZU)1 (0.2 g, 0.544 mmol) and 2-amino-6-chloropurine (0.25 g, 1.51 mmol) in acetonitrile (6 mL) was added BSA (2 ml, 1.51 mmol). The reaction mixture was heated to 85° C. for 30 min, then cooled to 0° C. TMSOTf (0.51 mL) was added. The reaction mixture was heated to 85° C. overnight, cooled to room temperature, poured into saturated sodium bicarbonate, extracted with ethyl acetate (20 mL×2), dried, conc., and purified by flash column chromatography with ethyl acetate:hexane=1:1 to get the desired compound 0.1 g. 43%. It contained two isomers (alpha:beta=1.1:1)

Workup

  1. additionwas added BSA (2 ml, 1.51 mmol)
  2. temperaturecooled to 0° C
  3. temperatureThe reaction mixture was heated to 85° C. overnight
  4. temperaturecooled to room temperature
  5. extractionextracted with ethyl acetate (20 mL×2)
  6. customdried
  7. customconc., and purified by flash column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-a6556d6e20e74f10a54dcc307dabf09e
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815829B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes