[H-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][NH:7][C:6]2=[N:10][CH:11]=[CH:12][C:5]=12.[H][H].[C:15]([O:18][CH2:19][CH2:20][O:21][CH2:22]Br)(=[O:17])[CH3:16]>CN(C=O)C.O>[Cl:3][C:4]1[C:5]2[CH:12]=[CH:11][N:10]([CH2:22][O:21][CH2:20][CH2:19][O:18][C:15](=[O:17])[CH3:16])[C:6]=2[N:7]=[CH:8][N:9]=1
Sodium hydride (0.09 g, 60% in mineral oil) was added to a solution of 4-chloropyrrolo[2,3-d]pyrimidine (1) in dry DMF (6 mL) in small portions at 0-5 degrees C under a nitrogen atomosphere. When all hydrogen evolution has ceased, 2-acetoxyethoxymethyl bromide (2) (0.45 g) was added, dropwise with stirring, at room temperature. The reaction mixture was then stirred at room temperature for an additional 3 hours. After that period of time, water (50 mL) was added and the product was extracted with ethylacetate. The ethylacetate layer was separated, washed with cold water, dried over anhydrous, Na2SO4 and the solvent then evaporated under reduced pressure and temperature to afford a thick syrup. This syrup was applied to the top of a silica gel column (20×2 cm) and the column was eluted with 1% MeOH in CHCl3. All the fractions containing UV absorbing material were combined and the solvent from these fractions was evaporated to yield a colorless syrup was crystallized from methanol as colorless needles to yield 0.21 g of 3 (40.2%), mp 67-88 degrees C. 1H-NMR (DMSO-d6) δ: 8.5 (s, 1, C2-H), 7.88 (d, 1, J=3.5 Hz, C6-H), 6.72 (d, 1, J=3.6 Hz, C5-H), 5.7 (s, 2, N7-CH2), 4.03 (m, 2, OCH2), 3.52 (m, 2, CH2), 1.92 (s, 3, OAc): UVλmax nm (ε×104); (pH 7) 223 (1.2), 276 (2.4); (pH 1) 225 (1.2), 274 (0.25); (pH 11) 227 (0.8), 276 (0.2).
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