Hydrochloric Acid → (S)-2,5-dichloro-N-(4-(morpholin-2-yl)phenyl)pyrimidin-4-amine hydrochloride

HRID 2403326Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:11][CH:10]=2)[C:5]([Cl:28])=[CH:4][N:3]=1.Cl.CCOCC>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C@@H:15]3[O:20][CH2:19][CH2:18][NH:17][CH2:16]3)=[CH:13][CH:14]=2)[C:5]([Cl:28])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(S)-tert-Butyl 2-(4-(2,5-dichloropyrimidin-4-ylamino)phenyl)morpholine-4-carboxylate (45 mg, 0.106 mmol) was dissolved in dioxane (0.5 ml) and a solution of HCl in dioxane (4 M, 0.3 ml, 1.27 mmol) was added. The reaction mixture was stirred at 60° C. for 2 hours. After cooling, ether (2 ml) was added and the solid was filtered off. It was washed with ether and dried in vacuo to afford (S)-2,5-dichloro-N-(4-(morpholin-2-yl)phenyl)pyrimidin-4-amine hydrochloride (38 mg, 99%) as a white solid. MS (ISP): 325.1 ([{35Cl}M+H]+), 327.1 ([{37Cl}M+H]+).

Workup

temperatureAfter cooling
filtrationthe solid was filtered off
washIt was washed with ether
customdried in vacuo

Sources & evidence

ORD record: ord-84b5f87284ea4bc09f78af45ea163cc2
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802673B2

Reaction notes

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