Triethylamine → HCID 118390079, compound

HRID 1478076Notes

Reaction equation

[CH3:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:23][CH:19]3[CH2:20][NH:21][CH2:22][CH:18]3[CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.Cl[C:25]1[N:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=1.CCN(CC)CC>C(Cl)Cl.CO>[CH3:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:23][CH:19]3[CH2:20][N:21]([C:25]4[CH:26]=[CH:27][C:28]([C:31]#[N:32])=[CH:29][N:30]=4)[CH2:22][CH:18]3[CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 5-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine (112.0 mg, 0.36 mmol) and 6-chloropyridine-3-carbonitrile (102.5 mg, 0.74 mmol) in a mixture of DCM (5 mL) and MeOH (5 mL) was added Et3N (200.7 mg, 1.98 mmol). The reaction mixture was stirred at 45° C. overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40) to give the title compound as a beige solid (0.12 g, 81%).

Workup

concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40)

Sources & evidence

ORD record: ord-9291a359a0184c52978391f3c09ae818
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

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