4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 5-Chloro-7-morpholino-2-(6-morpholinopyridin-3-yl)thiazolo[5,4-d]pyrimidine

HRID 1692777Notes

Reaction equation

HRID 1692777 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]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[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:31]=[N:30][C:29]([N:32]4[CH2:33][CH2:34][O:35][CH2:36][CH2:37]4)=[CH:28][CH:27]=3)[S:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 252102844-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine

Product 1

HCID 866300735-Chloro-7-morpholino-2-(6-morpholinopyridin-3-yl)thiazolo[5,4-d]pyrimidine

Procedure

4-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine 18 was reacted with 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine via General Procedure A to give crude 5-chloro-7-morpholino-2-(6-morpholinopyridin-3-yl)thiazolo[5,4-d]pyrimidine, 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 123 after purification by reverse HPLC. MS (Q1) 478 (M+)

Sources & evidence

ORD record
ord-3cc654ddbcda42a69f907df3fe368aed
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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