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

HRID 876018Notes

Reaction equation

HRID 876018 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c98892028d18415fac999966255d2cdd
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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