tert-Butyldimethylsilyl chloride → HCID 10618349, compound

HRID 1359436Notes

Reaction equation

HRID 1359436 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[C:15]2[C:14]([Cl:16])=[N:13][C:12]([S:17][CH3:18])=[N:11][C:10]=2[NH:9][CH:8]=1)(=O)C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CO>[Si:19]([O:4][CH2:5][CH2:6][C:7]1[C:15]2[C:14]([Cl:16])=[N:13][C:12]([S:17][CH3:18])=[N:11][C:10]=2[NH:9][CH:8]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 10541163HCID 10541163, compound

Product 1

HCID 10618349HCID 10618349, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2-Acetoxyethyl)-4-chloro-2-methylsulfanyl-7H-pyrrolo[2,3-d]pyrimidine 2.5 (750 mg, 1.66 mmol) was de-acetylated with methanol-aq ammonia (100 ml) and dried by co-evaporation with dry pyridine. The residue was dissolved in dry pyridine (80 ml) and tert-butyldimethylsilyl chloride (598 mg, 3.94 mmol) added. The solution was stirred overnight, evaporated, and residual pyridine removed by co-evaporation with water (2×20 ml). The residue was dissolved in chloroform (500 ml), washed with saturated aq. sodium bicarbonate solution (100 ml), dried (Na2SO4) and evaporated. The crude product was purified by silica gel chomatography (32×400 mm) eluting with chloroform to give a white solid, 826 mg, 88%. Rf (in C) 0.43; δH(d6-DMSO) 12.10 (1 H, br s, NH), 7.28 (1 H, s, 6-H), 3.81 (2 H, t J 7.0, O—CH2), 2.96 (2 H, t J 7.0, O—CH2CH2), 2.53 (3 H, s, CH3), 0.83 (9 H, s, 3×CH3), −0.05 (6 H, s, 2×CH3).

Workup

  1. dry with materialdried by co-evaporation with dry pyridine
  2. dissolutionThe residue was dissolved in dry pyridine (80 ml)
  3. customevaporated
  4. customresidual pyridine removed by co-evaporation with water (2×20 ml)
  5. dissolutionThe residue was dissolved in chloroform (500 ml)
  6. washwashed with saturated aq. sodium bicarbonate solution (100 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe crude product was purified by silica gel chomatography (32×400 mm)
  10. washeluting with chloroform
  11. customto give a white solid, 826 mg, 88%

Sources & evidence

ORD record
ord-b9802e293d5c459bb7dcc452d99ff2be
Source dataset
uspto-grants-2003_07
Patent number
US06600028B1

Reaction notes

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