Tetrahydrofuran → 4-Methyl-7H-pyrrolo(2,3-d)pyrimidine

HRID 222180Notes

Reaction equation

HRID 222180 reaction equation
[Cl-].[Mg+2].[Cl-].Cl[C:5]1[N:10]=[CH:9][NH:8][C:7]2=[N:11][CH:12]=[CH:13][C:6]=12.[Cl-].[NH4+].[CH2:16]1COCC1>>[CH3:16][C:5]1[C:6]2[CH:13]=[CH:12][NH:11][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 5360315Magnesium ChlorideHCID 178418725HCID 178418725, compound

Product 1

HCID 513419594-Methyl-7H-pyrrolo(2,3-d)pyrimidineYield 69%

Procedure

A 3.00 M solution of magnesium chloride in THF (13.0 mL, 39.0 mmol) was added dropwise to a stirred solution of 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (2.50 g, 16.3 mmol) and ferric acetylacetonate (700. mg 1.98 mmol) in THF (30.0 mL) under an atmosphere of argon. The resulting reaction mixture was stirred at rt for 8 h. The mixture was poured onto a mixture of ice (100 mL) and ammonium chloride (1.00 g) and the mixture was extracted with chloroform. Volatiles were removed in vacuo, and C-18 column chromatography eluting with a gradient of 0 to 60% AcCN in water with 0.1% AA afforded the title compound (1.50 g, 69%). LC/MS: Rt=0.94 min, ES+ 134 (AA standard).

Workup

  1. customThe resulting reaction mixture
  2. extractionthe mixture was extracted with chloroform
  3. customVolatiles were removed in vacuo, and C-18 column chromatography
  4. washeluting with a gradient of 0 to 60% AcCN in water with 0.1% AA

Sources & evidence

ORD record
ord-22d6479e61fe4995938f26ec7de4ceb4
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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