4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → 6-chloro-2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidine

HRID 2098640Notes

Reaction equation

HRID 2098640 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([Cl:11])=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:26]2[CH:34]=[CH:33][CH:32]=[C:31]3[C:27]=2[CH:28]=[N:29][NH:30]3)O1>>[Cl:11][C:9]1[S:10][C:5]2[C:4]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:3][C:2]([C:26]3[CH:34]=[CH:33][CH:32]=[C:31]4[C:27]=3[CH:28]=[N:29][NH:30]4)=[N:7][C:6]=2[CH:8]=1

Participants

3

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595930962,6-Dichloro-4-morpholinothieno[3,2-d]pyrimidine

Product 1

HCID 595929106-chloro-2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidine

Procedure

40 mg of 2,6-dichloro-4-morpholinothieno[3,2-d]pyrimidine was coupled to 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 via General Procedure A. The product was purified by reverse phase HPLC to yield 4.4 mg of 134. MS (Q1) 372 (M)+

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-538cd07417aa47058127036605bb136e
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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