Water → HCID 14221931, compound

HRID 1073099Notes

Reaction equation

HRID 1073099 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[C:11]2[CH:18]=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][O:23][C:24](=[O:26])[CH3:25])[C:12]=2[N:13]=[CH:14][N:15]=1.O>C(Cl)Cl>[Cl:9][C:10]1[C:11]2[C:18]([Cl:1])=[CH:17][N:16]([CH2:19][O:20][CH2:21][CH2:22][O:23][C:24](=[O:26])[CH3:25])[C:12]=2[N:13]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 14221930HCID 14221930, compound

Product 1

HCID 14221931HCID 14221931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide was added to a solution of 4-chloro-7-(2-acetoxyethoxymethyl)pyrrolo[2,3-d]pyrimidine (3) (0.35 g) in dry methylene chloride (15 mL). The reaction mixture was stirred at room temperature for 8 days. At that time, TLC established a complete disappearance of starting material. Water (50 mL) was added to the mixture and the product was extracted with CHCl3 (3+30 mL). The chloroform extracts were combined and washed with water, then dried over anhydrous Na2SO4. The solvent was removed at 40° C. in vacuo and the resulting thick syrup was subjected to column chromatography. Elution of the silica gel column (15×2 cm) with benzene; chloroform (1:1), yielded a colorless oil (single spot on TLC) after evaporation of all the UV absorbing fractions at a reduced temperature and pressure, which was crystallized from ethyl alcohol to afford colorless needles of the acetylated intermediate, (7a, 0.23 g) (59.95%). 4,5-Dichloro-7-(2-acetoxyethoxymethyl)pyrrolo[2,3-d]pyrimidine (7a, 0.31 g) was then dissolved in dry methanol (15 mL) and to this solution was added methanol which had previously been saturated with ammonia at 0° C. (25 mL). The reaction mixture was stirred in a pressure bottle at room temperature for 20 hours. The solvent was evaporated at 30° C. in vacuo and the semi-solid mass was subjected to column chromatography. Elution of the product from a silica gel column (15×2 cm) with 2% meOH in CHCl3 yielded a colorless compound, after evaporation of all the appropriate UV absorbing fractions.

Workup

  1. extractionthe product was extracted with CHCl3 (3+30 mL)
  2. washwashed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. customThe solvent was removed at 40° C. in vacuo
  5. washElution of the silica gel column (15×2 cm) with benzene
  6. customchloroform (1:1), yielded a colorless oil (single spot on TLC)
  7. customafter evaporation of all the UV
  8. customabsorbing fractions at a reduced temperature and pressure, which
  9. customwas crystallized from ethyl alcohol

Sources & evidence

ORD record
ord-1c319c8436f04910831c11d755959076
Source dataset
uspto-grants-1990_11
Patent number
US04968686

Reaction notes

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