Trimethylsilyl triflate → HCID 137010181, compound

HRID 2205177Notes

Reaction equation

HRID 2205177 reaction equation
[O:1]=[C:2]1[NH:10][C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[N:8][C:7]2[NH:6][CH:5]=[N:4][C:3]1=2.C(O[CH:21]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:24]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@:23]([CH2:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([CH:38]([F:40])[F:39])[O:22]1)(=O)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.C([O-])(O)=O.[Na+]>CC#N>[C:27]([O:26][C@@H:25]1[C@H:24]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@:23]([CH2:41][O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([CH:38]([F:39])[F:40])[O:22][C@H:21]1[N:6]1[CH:5]=[N:4][C:3]2[C:2](=[O:1])[NH:10][C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:14])[CH3:15])=[N:8][C:7]1=2)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 131735802HCID 131735802, compoundHCID 178454493HCID 178454493, compound

Product 1

HCID 137010181HCID 137010181, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of compound N-(6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide (0.57 g, 2.58 mmol) in anhydrous CH3CN (50 mL) was added BSA (1.26 mL, 5.17 mmol) portion-wise while maintaining the reaction temperature at 25° C. Then the reaction was stirred at 40° C. for 1 h until a clear solution persisted. Compound 5 (0.6 g, 1.29 mmol) in CH3CN (5 mL) was added into the mixture at 0° C. followed by TMSOTf (0.94 mL, 5.17 mmol). The mixture was stirred at 40° C. for 2 h and then poured into saturated NaHCO3 solution (10 mL) at 0° C., extracted with ethyl acetate, washed with water, brine solution, dried over Na2SO4 and evaporated to dryness under reduced pressure. The crude compound was purified by silica gel chromatography [petroleum ether:ethyl acetate (5:1 to 1:1)] to provide the product 21 as a white foam (0.5 g, 60%). LC-MS: (M+H)+=626

Workup

  1. stirringThe mixture was stirred at 40° C. for 2 h
  2. extractionextracted with ethyl acetate
  3. washwashed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness under reduced pressure
  6. customThe crude compound was purified by silica gel chromatography [petroleum ether:ethyl acetate (5:1 to 1:1)]

Sources & evidence

ORD record
ord-372499770dc44153b91264f3c6e14510
Source dataset
uspto-grants-2016_06
Patent number
US09370569B2

Reaction notes

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