Sodium hydride → 1-(4-Amino-pyrido[3,2-d]pyrimidin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one

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Reaction Steps

3,6,6-Trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.181, 32 mg) is dissolved in 1 mL DMF. To this solution is added sodium hydride (60% suspension in mineral oil, 0.229 mmol, 9.18 mg) and the mixture is stirred at rt for 5 min. and then 7-Fluoro-pyrido[3,2-d]pyrimidin-4-ylamine (0.164 mmol, 27 mg) is added. The reaction mixture is stirred at 50° C. for 22 h. The reaction mixture is cooled and quenched by pouring into 20 mL sat. NH4Cl aq. and extracted 3 times with 5 mL CH2Cl2. The combined organics are dried with Na2SO4, concentrated, and purified by silica gel chromatography on Biotage using a gradient of 0-15% MeOH in DCM. 1-(4-Amino-pyrido[3,2-d]pyrimidin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one is isolated (12 mg, LC/MS m/z=322 [M+H]+) as a white powder.

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