5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → 2-(4-morpholino-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)propan-2-ol

HRID 2098811Notes

Reaction equation

HRID 2098811 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[CH:10]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[C:31]3[CH:37]=[CH:36][NH:35][C:32]3=[N:33][CH:34]=2)O1>>[O:18]1[CH2:19][CH2:20][N:15]([C:4]2[C:5]3[CH:10]=[C:9]([C:11]([OH:14])([CH3:13])[CH3:12])[S:8][C:6]=3[N:7]=[C:2]([C:29]3[CH:30]=[C:31]4[CH:37]=[CH:36][NH:35][C:32]4=[N:33][CH:34]=3)[N:3]=2)[CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 866184422-(2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol

Product 1

HCID 595929832-(4-morpholino-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl)propan-2-ol

Procedure

2-(2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)propan-2-ol (100) mg was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine via General Procedure A to give 120 mg of 351 following reverse phase HPLC purification. MS (Q1) 396.2 (M)+

Workup

  1. customto give
  2. custom120 mg of 351 following reverse phase HPLC purification

Sources & evidence

ORD record
ord-cf91d48d59fa4bbbbb537eb00a2510ef
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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