Sodium Bicarbonate → HCID 11231258, compound
Reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]3O)[C:6]=2[N:7]=1.O.CC#N.C[C:26](OC(C(Br)=O)(C)C)=[O:27].C([O-])(O)=O.[Na+]>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([O:27][CH3:26])[C:5]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@H:14]4[O:15][C@@H:12]34)[C:6]=2[N:7]=1Participants
Procedure
To a mixture of 2-amino-7-(β-D-ribofuranosyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.8 g, 6.0 mmol) in acetonitrile (80 mL) were added a solution of H2O/CH3CN (1:9, 1.08 mL) and then a-acetoxyisobutyryl bromide (3.5 mL, 24 mmol). After 2 h stirring at room temperature, saturated aqueous NaHCO3 (170 mL) was added and the mixture was extracted with EtOAc (300+200 mL). The combined organic phase was washed with brine (100 mL), dried (Na2SO4) and evaporated to a pale yellow foamy residue. This was suspended in anhydrous MeOH (80 mL) and stirred overnight with 25 mL of DOWEX OH− resin (previously washed with anhydrous MeOH). The resin was filtered, washed thoroughly with MeOH and the combined filtrate evaporated to give a pale yellow foam (1.92 g).
Workup
- extractionthe mixture was extracted with EtOAc (300+200 mL)
- washThe combined organic phase was washed with brine (100 mL)
- dry with materialdried (Na2SO4)
- customevaporated to a pale yellow foamy residue
- stirringstirred overnight with 25 mL of DOWEX OH− resin (
- washpreviously washed with anhydrous MeOH)
- filtrationThe resin was filtered
- washwashed thoroughly with MeOH
- customthe combined filtrate evaporated
Sources & evidence
- ORD record
- ord-c291aef4d1f44868be44e3e153db9259
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105499B2
Reaction notes
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