Water ethanol → 4-Chloro-5-iodo-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 417835Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[C:17]([I:18])=[CH:16][N:15]([CH2:19][C:20]3[C:25]([CH3:26])=[C:24]([O:27][CH3:28])[C:23]([CH3:29])=[CH:22][N:21]=3)[C:4]=2[N:5]=[C:6]([NH:8]C(=O)C(C)(C)C)[N:7]=1.CCO.O>[Cl-].[Cl-].[Zn+2].O>[Cl:1][C:2]1[C:3]2[C:17]([I:18])=[CH:16][N:15]([CH2:19][C:20]3[C:25]([CH3:26])=[C:24]([O:27][CH3:28])[C:23]([CH3:29])=[CH:22][N:21]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-[4-chloro-5-iodo-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl]-2,2-dimethyl-propionamide (1.0 g, 1.89 mmol), ZnCl2 (1.29 g, 9.47 mol, 5.0 eq.), and EtOH/H2O solution (25 mL, volumetric ratio 100:5) was stirred at 80° C. overnight. The reaction mixture poured into water, and the solid was collected by filtration, washed with water (10 mL×3), and recrystallized from MeOH to give the title product (0.67 g, 85% yield; HPLC purity 98%). tR: 5.39 min. 1H-NMR (DMSO-d6) δ 8.07 (s, 1H), 7.28 (s, 1H), 6.75 (br. s, 2H), 5.29 (s, 2H), 3.73 (s, 3H), 2.26 (s, 3H), 2.17 (s, 3H).

Workup

filtrationthe solid was collected by filtration
washwashed with water (10 mL×3)
customrecrystallized from MeOH

Sources & evidence

ORD record: ord-0c778d872ea64c40805b3d95bc05c374
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093229B2

Reaction notes

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