Imidazole → HCID 10618349, compound

HRID 1359434Notes

Reaction equation

HRID 1359434 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:11]([Cl:13])=[N:10][C:9]([S:14][CH3:15])=[N:8][C:7]=2[NH:6][CH:5]=1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C>[Cl:13][C:11]1[C:12]2[C:4]([CH2:3][CH2:2][O:1][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:5][NH:6][C:7]=2[N:8]=[C:9]([S:14][CH3:15])[N:10]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10490451HCID 10490451, compound

Product 1

HCID 10618349HCID 10618349, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The hydroxyethyl pyrrolopyrimidine (1.4) (1.91 g, 7.8 mmol) was dissolved in DMF (25 ml) and tert-butyldimethylsilyl chloride (1.77 g, 11.7 mmol) and imidazole (1.6 g, 23.5 mmol) added and the solution stirred at room temperature for 6 hours. The solvent was removed and the product dissolved in chloroform, washed with water and the solvent evaporated. The product was precipitated by trituration with methanol, filtered and dried to give an off-white solid. A second fraction was obtained by concentration of the mother liquors. Yield 2.51 g, 89%. δH −0.07 (6H, s, 2×CH3), 0.80 (9H, s, C(CH3)3), 2.52 (3H, s, SCH3), 2.94 (2H, t, J 7.0 Hz, OCH2CH2), 3.78 (2H, t, J 7.0 Hz, OCH2), 7.29 (1H, s, H6), 12.10 (1H, s, NH) ppm.

Workup

  1. customThe solvent was removed
  2. dissolutionthe product dissolved in chloroform
  3. washwashed with water
  4. customthe solvent evaporated
  5. customThe product was precipitated by trituration with methanol
  6. filtrationfiltered
  7. customdried
  8. customto give an off-white solid
  9. customA second fraction was obtained by concentration of the mother liquors

Sources & evidence

ORD record
ord-5693f55ccb9b4f3da93e06461d06afb0
Source dataset
uspto-grants-2003_07
Patent number
US06600028B1

Reaction notes

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