1-(2,4-Dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanone → Tert-butyl 4-(4-(5-acetyl-4-chloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-2-ylamino)-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate

HRID 2046956Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 1-(2,4-dichloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-5-yl)ethanone (113 mg, 0.29 mmol) in EtOH (2 mL) was added tert-butyl-4-(4-amino-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate (203 mg, 0.58 mmol), and the reaction mixture was heated at 130° C. for 30 min The reaction was concentrated in vacuo, followed by purification by silica gel chromatography (EtOAC/Hexanes: 3/7) to afford Tert-butyl 4-(4-(5-acetyl-4-chloro-6-(2-(isopropylsulfonyl)phenylamino)pyrimidin-2-ylamino)-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate. MS (ES+): 700.3 (MH+).

Workup

concentrationwas concentrated in vacuo
customfollowed by purification by silica gel chromatography (EtOAC/Hexanes: 3/7)

Sources & evidence

ORD record: ord-bae8ed3cc5c14a7bae4bae7b1648c704
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592432B2

Reaction notes

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