반응 #162503

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(1S)-1-(6-(3,5-Dimethyl-1H-pyrazol-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine hydrochloride

2,4-diamino-6-chloropyrimidine-5-carbonitrile

N-ethyl-N-isopropylpropan-2-amine

→

title compound

수율 55.0%

2,4-Diamino-6-(((1S)-1-(6-(3,5-dimethyl-1H-pyrazol-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)pyrimidine-5-carbonitrile

수율 55.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   기타purified by preparative HPLC (basic mode)
3. 3
   세척eluting with 30% ACN in water
4. 4
   workup.ADDITIONThe fractions containing the desired product
5. 5
   농축concentrated

실험 절차

(1S)-1-(6-(3,5-Dimethyl-1H-pyrazol-4-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine hydrochloride (123 mg, 0.403 mmol), 2,4-diamino-6-chloropyrimidine-5-carbonitrile (82 mg, 0.484 mmol), and N-ethyl-N-isopropylpropan-2-amine (211 μL, 1.21 mmol) were combined in acetonitrile (4030 μL). The reaction mixture was heated in a microwave reactor at 120° C. for 2 hours and then concentrated in vacuo. The residue was taken up in DMF and purified by preparative HPLC (basic mode) eluting with 30% ACN in water. The fractions containing the desired product were combined, concentrated, and lyophilized to give the title compound as an off-white solid (89 mg, 55%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.12 (d, J=6.35 Hz, 3 H), 1.92 (br s, 3 H), 2.06 (br s, 3 H), 3.82 (s, 3H), 5.20 (br s, 1 H), 6.43 (br s, 2 H), 6.53-6.60 (m, 3 H), 6.96 (br s, 1 H), 7.62-7.69 (m, 2H), 12.36 (br s, 1 H); ESI-MS m/z [M+H]+ calc'd for C26H22N10, 403; found 403.

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