5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 86630076, compound

HRID 1692781Notes

Reaction equation

HRID 1692781 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[N:10]=[C:9](I)[S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=2)O1>>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[N:10]=[C:9]([C:26]3[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=3)[S:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 252102844-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine

Product 1

HCID 86630076HCID 86630076, compound

Procedure

4-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine 18 was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine via General Procedure A to give crude 5-(5-chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)pyridin-2-amine, which was then reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine via General Procedure A again to give 127 after purification by reverse HPLC. MS (Q1) 408 (M+)

Sources & evidence

ORD record
ord-05ad7f275ad84787b4f3d4c14ea97b4b
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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