Diisopropylethylamine → HCID 86762629, compound

HRID 2409081Notes

Reaction equation

[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[C:6]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:5]=12.Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:33]=[C:32]([CH:34]3[CH2:36][CH2:35]3)[NH:31][N:30]=2)[CH:25]=[CH:24][N:23]=1.CCN(C(C)C)C(C)C>CC(C(O)C(C)C)C>[CH:34]1([C:32]2[NH:31][N:30]=[C:29]([NH:28][C:26]3[CH:25]=[CH:24][N:23]=[C:22]([N:2]([CH3:1])[CH2:3][C:4]4[CH:9]=[N:8][CH:7]=[C:6]5[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:5]=45)[N:27]=3)[CH:33]=2)[CH2:36][CH2:35]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of N-methyl(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methanamine (110 mg, 0.38 mmol), 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (107 mg, 0.454 mmol), DIPEA (146 mg, 1.134 mmol) in 2,4-dimethylpentan-3-ol (2.0 mL) in a sealed tube was heated at 140° C. overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with DCM/MeOH (10:1) to afford 108 mg of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methyl-N2-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)pyrimidine-2,4-diamine as a yellow solid. MS (ESI): m/z=491.2 [M+1]+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customThe residue was purified by SiO2 chromatography
washeluting with DCM/MeOH (10:1)

Sources & evidence

ORD record: ord-3909ca44724f4f278a39144a8838206b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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