Tetrahydrofuran → 2-trimethylsilanyl-ethoxymethyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 889589

Reaction equation

HRID 889589 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[H-].[Na+].ClCOCC[Si:17]([CH3:20])([CH3:19])[CH3:18].C1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH3:18][Si:17]([CH3:20])([CH3:19])[C:2]1[N:3]=[C:4]([CH2:25][O:24][CH2:23][CH3:22])[C:5]2[CH:9]=[CH:8][NH:7][C:6]=2[N:1]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 2615917H-Pyrrolo(2,3-d)pyrimidineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 866174812-trimethylsilanyl-ethoxymethyl-7H-pyrrolo[2,3-d]pyrimidine

Procedure

7H-Pyrrolo[2,3-d]pyrimidine (1.16 g, 9.74 mmol), was dissolved in 100 ml anhydrous THF under N2. At 0° C., a 60% dispersion of NaH 0.51 g in mineral oil was added. The mixture was stirred at ambient temperature and 2.93 ml (9.8 mmol) (2-chloromethoxy-ethyl)-trimethyl-silane dissolved in 15 ml anhydrous THF was added. The reaction mixture was stirred at room temperature for 2 hour and subsequently concentrated in vacuo. Ethyl acetate was added to the mixture and the organic layer was washed three times with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (diethyl ether) to afford 7-(2-trimethylsilanyl-ethoxymethyl-7H-pyrrolo[2,3-d]pyrimidine (compound 91), (amorphous, 0.84 g, 35%). 1H-NMR (400 MHz, CDCl3): δ 9.1 (bs, 1H), 9.0 (bs, 1H), 7.43 (bd, J=4 Hz, 1H), 6.68 (bd, J=4 Hz, 1H), 5.73 (s, 1H), 3.6 (t, J=8 Hz, 2H), 0.97 (t, J=8 Hz, 2H), 0.1 (s, 9H).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for 2 hour
  3. concentrationsubsequently concentrated in vacuo
  4. additionEthyl acetate was added to the mixture
  5. washthe organic layer was washed three times with a saturated NaHCO3 solution
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by flash chromatography (diethyl ether)

Sources & evidence

ORD record
ord-4c1ad12326724c35bd87d949d9632358
Source dataset
uspto-grants-2012_08
Patent number
US08252930B2

Linked notes

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