Sodium Hydroxide → 2-(2,4-Dichloro-7h-pyrrolo[2,3-d]pyrimidin-6-yl)propan-2-ol
Reaction equation
C1(S([N:10]2[C:14]3[N:15]=[C:16]([Cl:20])[N:17]=[C:18]([Cl:19])[C:13]=3[CH:12]=[C:11]2[C:21]([OH:24])([CH3:23])[CH3:22])(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)(C)C.O>[Cl:20][C:16]1[N:17]=[C:18]([Cl:19])[C:13]2[CH:12]=[C:11]([C:21]([OH:24])([CH3:22])[CH3:23])[NH:10][C:14]=2[N:15]=1Participants
Procedure
Lithium diisopropylamide (2 mL, 4.0 mmol, 2 M in THF) was added dropwise to a solution of 7-benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (656 mg, 2.0 mmol) in anhydrous THF (15 mL) at −78° C. The resulting solution was stirred at −78° C. for 90 min, then acetone (0.4 mL, 5.5 mmol) was added and the reaction mixture was stirred at −78° C. for 30 min. The reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated in vacuo affording 2-(7-benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol. To a solution of 2-(7-benzenesulfonyl-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol (2 mmol) in a mixture of isopropyl alcohol (11 mL) and water (3 mL) was added sodium hydroxide (6 mL, 36 mmol, 6M aqueous solution). The resulting mixture was stirred at RT for 2 h, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0 to 40% ethyl acetate in cyclohexane) affording 2-(2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-propan-2-ol (304 mg, 64%). LCMS (method A): RT=2.70 min, [M]−=244/246.
Workup
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by column chromatography (SiO2, gradient 0 to 40% ethyl acetate in cyclohexane)
Sources & evidence
- ORD record
- ord-8072552a31c94e10ad0017c69000b5b2
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883799B2
Reaction notes
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