Sodium Iodide → N2-(4-(1-(3-(azetidin-1-ylsulfonyl)propyl)piperidin-4-yl)-2,5-dimethylphenyl)-5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 536393Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:11][C:10]=2[CH3:22])=[N:6][CH:7]=1.Cl[CH2:31][CH2:32][CH2:33][S:34]([N:37]1[CH2:40][CH2:39][CH2:38]1)(=[O:36])=[O:35].[I-].[Na+]>CN1C(=O)CCC1>[N:37]1([S:34]([CH2:33][CH2:32][CH2:31][N:19]2[CH2:20][CH2:21][CH:16]([C:12]3[C:13]([CH3:15])=[CH:14][C:9]([NH:8][C:5]4[N:4]=[C:3]([NH:23][C:24]5[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=5)[C:2]([Cl:1])=[CH:7][N:6]=4)=[C:10]([CH3:22])[CH:11]=3)[CH2:17][CH2:18]2)(=[O:36])=[O:35])[CH2:40][CH2:39][CH2:38]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 5-chloro-N2-(2,5-dimethyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (42 mg, 0.1 mmol), 1-(3-chloropropylsulfonyl)azetidine (Step 1, 0.1 mmol), TEA (70 μL) and sodium iodide (150 mg) in NMP (1 mL) was placed in a sealed vial which was heated in a microwave for 30 min at 150° C. The reaction was purified by RP-HPLC to give N2-(4-(1-(3-(azetidin-1-ylsulfonyl)propyl)piperidin-4-yl)-2,5-dimethylphenyl)-5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as a white powder; ESMS m/z 573.3 (M+H+).

Workup

customThe reaction was purified by RP-HPLC

Sources & evidence

ORD record: ord-93e5731c3a6747a282b83f889b2d3416
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859574B2

Reaction notes

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