Sodium hydride → 2-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-pyridyl cyanide

HRID 897539Notes

Reaction equation

[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[NH:10][N:11]=[C:12]([I:13])[C:5]=12.Cl[C:15]1[C:20]([C:21]#[N:22])=[CH:19][CH:18]=[CH:17][N:16]=1>CN(C=O)C>[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([C:15]3[C:20]([C:21]#[N:22])=[CH:19][CH:18]=[CH:17][N:16]=3)[N:11]=[C:12]([I:13])[C:5]=12

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 3.825 mmol, 153 mg) was added to a suspension of 4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (1.0 g, 3.825 mmol) in DMF (5 mL). After 10 min, 2-chloro-3-cyanopyridine (531 mg) was added and the reaction was heated at 60° C. for 16 h. The resulting dark mixture was poured into ice-water (50 mL) and the solid collected by filtration to afford 2-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-pyridyl cyanide as a brown solid (1.1 g, 79%); 1H NMR (DMSO-d6, 400 MHz) δ 7.82 (1H, m), 8.29 (1H, s), 8.64 (1H, m) and 8.93 (1H, m); RP-HPLC (Pecosphere, C18, 3 μm, 33×4.6 mm column, 0% to 100% acetonitrile in 50 mM ammonium acetate, buffered to pH 4.5, at 3.5 mL/min) Rt 2.16 min.

Workup

filtrationthe solid collected by filtration

Sources & evidence

ORD record: ord-d4d15c303727467daab7437b4db890b8
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921763B2

Reaction notes

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