(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanone → (4-Chloro-2-(2-isopropoxy-4-(1-(2-methoxyethyl)piperidin-4-yl)-5-methylphenylamino)-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanone

HRID 2046987Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[C:4]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[N:3]=1.[CH:30]([O:33][C:34]1[CH:40]=[C:39]([CH:41]2[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][O:49][CH3:50])[CH2:43][CH2:42]2)[C:38]([CH3:51])=[CH:37][C:35]=1[NH2:36])([CH3:32])[CH3:31]>CCN(C(C)C)C(C)C.CC(O)C>[Cl:8][C:6]1[C:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[C:4]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[N:3]=[C:2]([NH:36][C:35]2[CH:37]=[C:38]([CH3:51])[C:39]([CH:41]3[CH2:42][CH2:43][N:44]([CH2:47][CH2:48][O:49][CH3:50])[CH2:45][CH2:46]3)=[CH:40][C:34]=2[O:33][CH:30]([CH3:32])[CH3:31])[N:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a 10 mL microwave reaction tube, (2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanone (24.1 mg, 0.0548 mmol), 2-isopropoxy-4-(1-(2-methoxyethyl)piperidin-4-yl)-5-methylaniline (16.8 mg, 0.0548 mmol), 2-propanol (4 mL) and Hunig's Base (3 drops) were added successively. The resulting mixture was stirred at 150° C. for 2 hours by using a microwave machine. The reaction solution concentrated in vacuo to afford crude (4-chloro-2-(2-isopropoxy-4-(1-(2-methoxyethyl)piperidin-4-yl)-5-methylphenylamino)-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)(phenyl)methanone as a slightly yellow sticky oil. MS (ES+): 720.30 (MH+).

Workup

concentrationThe reaction solution concentrated in vacuo

Sources & evidence

ORD record: ord-b077da4f1ba64acdb3bbb865e82303a9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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