HCID 3010392, compound → 4-Amino-5-bromo-7-(2-hydroxyethoxymethyl)pyrrolo(2,3-d)pyrimidine
Reaction equation
Cl[C:2]1[C:3]2[C:10]([Br:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][OH:16])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:17].N>CO>[NH2:17][C:2]1[C:3]2[C:10]([Br:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][OH:16])[C:4]=2[N:5]=[CH:6][N:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 125 °C
Procedure
5-Bromo-4-chloro-7-(2-hydroxyethoxymethyl)pyrrolo [2,3-d]pyrimidine (8b, 0.7 g) was dissolved in dry methanol (10 mL) and methanol saturated with NH3 ammonia (40 mL) was then added to this solution. The reaction mixture was heated at 125 degrees C. in a sealed reaction vessel for 10 hours. The solvent was removed at 40 degrees under reduced pressure and the resulting solid was then subjected to column chromatography. Elution of the silica gel column (20×3 cm) with 5% MeOH in CHCl3 yielded a solid after evaporation of the appropriate UV absorbing fractions. This solid was recrystallized from CHCl3 to afford 11, 0.18 g (31.25%), mp 163-164 degrees C. 1H-NMR (DMSO-d6): δ 8.13 (s, 1, C2-H), 7.55 (s, 1, C6-H), 6.81 (bs, 2, exchangeable with D2O, NH2), 5.5 (s, 2, N7-CH2), 4.62 (m, 1, exchangeable with D2O, OH), 3.42 (m, 4, CH2): UVλmax nm (ε×104) (pH 7) 211 (1.9), 278 (0.9); (pH 1) 233 (2.0), 280 (0.94); (pH 11) 227 (0.9), 278 (0.95).
Workup
- customin a sealed reaction vessel for 10 hours
- customThe solvent was removed at 40 degrees under reduced pressure
- washElution of the silica gel column (20×3 cm) with 5% MeOH in CHCl3
- customyielded a solid
- customafter evaporation of the appropriate UV
- customabsorbing fractions
- customThis solid was recrystallized from CHCl3
Sources & evidence
- ORD record
- ord-08db7aaafa484f8cbc1374f3b6e95d24
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04927830
Reaction notes
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