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

HRID 876018노트

반응식

HRID 876018 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c98892028d18415fac999966255d2cdd
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

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