Dimethylformamide → HCID 54131015, compound

HRID 223166Notes

Reaction equation

HRID 223166 reaction equation
Cl[C:2]1[C:3]2[CH:14]=[CH:13][N:12]([C@@H:15]3[O:35][C@H:34]([CH2:36][O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@@H:25]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@@H:16]3[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:4]=2[N:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[N:7]=1.[CH2:45]([O:48]CC=C)[CH:46]=[CH2:47].[Na].CN(C=O)C>C(OCC)(=O)C>[CH2:45]([O:48][C:2]1[C:3]2[CH:14]=[CH:13][N:12]([C@@H:15]3[O:35][C@H:34]([CH2:36][O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@@H:25]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@@H:16]3[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:4]=2[N:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[N:7]=1)[CH:46]=[CH2:47]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22821689HCID 22821689, compoundHCID 86738583HCID 86738583, compound

Product 1

HCID 54131015HCID 54131015, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 10 g of 4chloro-2-methylsulfonyl-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine, 1.35 g of sodium allyloxide, and 50 ml of DMF is stirred at ambient temperature for 24 hours, evaporated in vacuo and coevaporated with xylenes. The residue is distributed between a mixture of ethyl acetate and water and the dried ethyl acetate extracts are evaporated in vacuo to provide crude product. Chromatography of this material over silica gel with ethyl acetate provides pure 4-allyloxy-2-methylsulfonyl-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine.

Workup

  1. customevaporated in vacuo
  2. additionThe residue is distributed between a mixture of ethyl acetate and water
  3. customthe dried ethyl acetate extracts are evaporated in vacuo
  4. customto provide crude product

Sources & evidence

ORD record
ord-1556cc2ae6c744fe89c24cbe1987d685
Source dataset
uspto-grants-1982_10
Patent number
US04352795

Reaction notes

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