Tetrahydrofuran → 9-Cyclopentyl-3-methoxy-9H-pyrimido[5',4':4,5]pyrrolo[2,3-c]pyridazin-7-amine

HRID 79194ノート

反応式

HRID 79194 の反応式
[CH:1]1([NH:6][C:7]2[C:12]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[N:16]=[N:15][C:14]=3OC)=[CH:11][N:10]=[C:9]([NH2:23])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.[H-].[Na+]>CO.C(Cl)Cl>[CH:1]1([N:6]2[C:14]3[N:15]=[N:16][C:17]([O:19][CH3:20])=[CH:18][C:13]=3[C:12]3[CH:11]=[N:10][C:9]([NH2:23])=[N:8][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67234657N4-Cyclopentyl-5-(3,6-dimethoxy-4-pyridazinyl)-2,4-pyrimidinediamine

生成物 1

HCID 583000759-Cyclopentyl-3-methoxy-9H-pyrimido[5',4':4,5]pyrrolo[2,3-c]pyridazin-7-amine収率 94.9%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

To a 35 mL microwave reaction vessel were placed with compound 316 (200 mg, 0.63 mmol) followed by THF and sodium hydride, (60% in mineral oil, 0.063 g, 1.6 mmol). The resulting mixture was stirred at room temperature for 10 min to allow gas release. Then the vessel was subjected to microwave reaction condition (60 min at 150° C.). The crude mixture was subjected to combi-flash column chromatography (methanol/DCM) to give compound 317 (0.17 g) as a light yellow solid (contaminated with mineral oil). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.97 (1 H, s), 7.57 (1 H, s), 7.28 (2 H, s), 5.28 (1 H, quin, J=8.7 Hz), 4.02 (3 H, s), 2.38-2.46 (2 H, m), 1.89-2.10 (4 H, m), 1.62-1.78 (2 H, m). LCMS-ESI (POS), M/Z, M+1: Found 285.1.

後処理

  1. customreaction condition (60 min at 150° C.)

出典と根拠

ORDレコード
ord-1d2f66b734fc498f9b70aa8e69eaa238
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

反応ノート

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