1,4-Dioxane → Ethyl 4-(3-fluoro-4-(2-(pyrrolidine-1-carboxamido)pyridin-4-yloxy)phenylamino)-2-(methylthio)pyrimidine-5-carboxylate

HRID 606145Notes

Reaction equation

[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[C:4]([F:23])[CH:3]=1.Cl[C:25]1[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][N:28]=[C:27]([S:36][CH3:37])[N:26]=1.C(N(C(C)C)C(C)C)C.O1CCOCC1>C(Cl)Cl.O>[F:23][C:4]1[CH:3]=[C:2]([NH:1][C:29]2[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][N:26]=[C:27]([S:36][CH3:37])[N:28]=2)[CH:22]=[CH:21][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:15])[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-(4-(4-amino-2-fluorophenoxy)pyridin-2-yl)pyrrolidine-1-carboxamide (0.158 g, 0.5 mmol), ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (0.2 g, 1.0 mmol), N-ethyl-N-isopropylpropan-2-amine (0.1 g, 1.0 mmol) in 1,4-dioxane (1 g, 11 mmol) was heated in microwave (CEM) at 60 W and 60° C. for 40 min. The resultant was diluted with DCM (15 mL) and water (10 mL). The organic layer was separated, dried over sodium sulfate, and concentrated. The residue was used for the next step without further purification.

Workup

customThe organic layer was separated
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was used for the next step without further purification

Sources & evidence

ORD record: ord-7ea7fab0a65243e49d53099c67c876e7
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915287B2

Reaction notes

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