Azane;hydrate → 7-(2-C-Ethynyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[C@:15]([C:17]#[CH:18])([OH:16])[C@H:14]([OH:19])[C@@H:13]([CH2:20][OH:21])[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:22].O>>[NH2:22][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@H:11]3[C@:15]([C:17]#[CH:18])([OH:16])[C@H:14]([OH:19])[C@@H:13]([CH2:20][OH:21])[O:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of (2R,3R,4R,5R)-2-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-hydroxymethyl-tetrahydrofuran-3,4-diol (198.0 mg, 0.64 mmol,) and NH3.H2O (30 mL) in a glass pressure tube is heated at 100° C. for 5 h. The reaction mixture is concentrated to dry and purified by flash chromatography (CH2Cl2:MeOH=80:20) to yield (2R,3R,4R,5R)-2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3-ethynyl-5-hydroxymethyl-tetrahydrofuran-3,4-diol as pale yellow solid. 1H NMR (300 MHz, MeOD): δ 8.07 (1H, s), 7.48 (1H, d, J=3.9 Hz), 6.58 (1H, d, J=3.6 Hz), 6.29 (1H, s), 4.49 (1H, d, J=8.4 Hz), 4.08-3.96 (2H, m), 3.90-3.75 (1H, m), 2.52 (1H, s). 1H NMR (300 MHz, DMSO-d6): δ 8.05 (1H, s), 7.41 (1H, d, J=3.6 Hz), 6.97 (2H, s), 6.55 (1H, d, J=3.6 Hz), 6.23 (1H, s), 6.16 (1H, s), 5.61 (1H, d, J=7.5 Hz), 5.13 (1H, t, J=4.9 Hz), 4.33 (1H, t, J=7.8 Hz), 3.90-3.70 (2H, m), 3.78-3.68 (1H, m), 3.01 (1H, s). 13C NMR (75 MHz, DMSO-d6): δ 157.4, 151.6, 150.1, 121.6, 102.4, 99.6, 89.6, 82.1, 81.8, 76.5, 75.8, 74.0, 59.7. ESI-MS: calcd. for C13H14N4O4 (290.1). found: 291.2.
Workup
- concentrationThe reaction mixture is concentrated
- customto dry
- custompurified by flash chromatography (CH2Cl2:MeOH=80:20)
Sources & evidence
- ORD record
- ord-54215b7d67814e89ae3fd9739c674def
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278282B2
Reaction notes
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