Bicarbonate Ion → HCID 178476611, compound

HRID 890863Notes

Reaction equation

HRID 890863 reaction equation
C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.C(O[CH:17]1[O:33][C@:32]([CH2:40]S(C)(=O)=O)([CH2:34][O:35][S:36]([CH3:39])(=[O:38])=[O:37])[C@@H:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])(=O)C.[NH2:45][C:46]1[N:54]=[C:53]2[C:49]([NH:50][CH:51]=[N:52]2)=[C:48]([Cl:55])[N:47]=1.C[Si]([O:60][S:61]([C:64](F)(F)F)(=[O:63])=[O:62])(C)C.C(=O)(O)[O-]>ClCCCl.C(O)(=O)C>[C:20]([O:19][C@@H:18]1[C@H:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]([CH2:34][O:35][S:36]([CH3:39])(=[O:37])=[O:38])([CH2:40][O:63][S:61]([CH3:64])(=[O:62])=[O:60])[O:33][C@H:17]1[N:47]1[C:48]([Cl:55])=[C:49]2[C:53](=[N:52][CH:51]=[N:50]2)[N:54]=[C:46]1[NH2:45])(=[O:22])[CH3:21]

Participants

8

Reactant 5

HCID 769Bicarbonate IonHCID 65367Trimethylsilyl triflateHCID 53603492-Amino-6-chloropurineHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 23597610HCID 23597610, compound

Product 1

HCID 178476611HCID 178476611, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

N,O-bis(trimethylsilyl)acetamide (29.6 g, 35 ml) was added to a stirred slurry of (3) (30 g, 58.8 mmol) and 2-amino-6-chloropurine (12 g, 70 mmol) in 1,2-dichloroethane (dried over sieves, 450 ml) and the mixture was refluxed for 40 min. to give a homogenous solution. The mixture was then removed from the heat and trimethylsilyltriflat (22 ml, 118 mmol) was added dropwise. The reaction mixture was refluxed for another 2 h. The reaction mixture was cooled to room temperature and a saturated aqueous solution of bicarbonate (400 ml) was added. The slurry was allowed to stir for 15 min, pH was adjusted to 7-8 using glacial acetic acid and the mixture was extracted with chloroform. The aqueous phase was extracted with AcOEt and chloroform and the organic phases were combined. The organic phase was washed with brine (2×250 ml) and bicarbonate (2×250 ml). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give compound (4) as a yellowish foam which expands during vacuum dessication

Workup

  1. temperaturethe mixture was refluxed for 40 min.
  2. customto give a homogenous solution
  3. customThe mixture was then removed from the
  4. temperatureheat
  5. temperatureThe reaction mixture was refluxed for another 2 h
  6. extractionthe mixture was extracted with chloroform
  7. extractionThe aqueous phase was extracted with AcOEt and chloroform
  8. washThe organic phase was washed with brine (2×250 ml) and bicarbonate (2×250 ml)
  9. dry with materialThe organic phase was dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ece58b30d736489d923ab08a0da54244
Source dataset
uspto-grants-2006_02
Patent number
US06998484B2

Reaction notes

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