Stannous Chloride → 1-(2,5-Diaminopyrimidin-4-yl)indazole-6-carbonitrile

HRID 1398491ノート

反応式

HRID 1398491 の反応式
[NH2:1][C:2]1[NH:7][CH:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[CH:10]=[N:9]2)[C:5]([N+:19]([O-])=O)=[CH:4][N:3]=1.[Sn](Cl)Cl>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[CH:10]=[N:9]2)[C:5]([NH2:19])=[CH:4][N:3]=1

参加物

4

反応物 2

HCID 24479Stannous ChlorideHCID 178509490HCID 178509490、化合物

生成物 1

HCID 601639861-(2,5-Diaminopyrimidin-4-yl)indazole-6-carbonitrile収率 11%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of 1-(2-amino-5-nitro-3,4-dihydropyrimidin-4-yl)-1H-indazole-6-carbonitrile (40% purity, 400 mg, 0.64 mmol) and tin (II) chloride (577 mg, 2.56 mmol) in ethanol (15 mL) was heated at 60° C. for 2 hr then at 70° C. for 3 hr. LC-MS (Method B) showed 11% desired product and 74% degradation. The reaction mixture was concentrated in vacuo. The residue was vigorously stirred with a mixture of saturated aqueous Rochelle salt (potassium sodium tartrate (20 mL), saturated aqueous NaHCO3 (20 mL) and EtOAc (30 mL) for 30 min. The EtOAc layer was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude was purified by column chromatography (Biotage) (100% EtOAc) to give the title compound as a pale yellow solid: 1H NMR (250 MHz, DMSO) δ 5.40 (2H, br. s.), 6.30 (2H, s), 7.69 (1H, dd, J=8.38, 1.22 Hz), 8.01-8.25 (2H, m), 8.62 (1H, d, J=0.76 Hz), 9.31 (1H, s); LC-MS: m/z=+252.0 (M+H)+.

出典と根拠

ORDレコード
ord-75f998548000435289e3e9e8444d9cee
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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