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

HRID 2262312Notes

Reaction equation

HRID 2262312 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]2[S:10][C:9]([C:11]3[N:12]=[C:13]([NH2:16])[S:14][CH:15]=3)=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[C:33]3[CH:39]=[CH:38][NH:37][C:34]3=[N:35][CH:36]=2)O1>>[O:20]1[CH2:21][CH2:22][N:17]([C:4]2[C:5]3[S:10][C:9]([C:11]4[N:12]=[C:13]([NH2:16])[S:14][CH:15]=4)=[CH:8][C:6]=3[N:7]=[C:2]([C:31]3[CH:32]=[C:33]4[CH:39]=[CH:38][NH:37][C:34]4=[N:35][CH:36]=3)[N:3]=2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 595929714-(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)thiazol-2-amine

Product 1

HCID 249689434-(4-morpholino-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl)thiazol-2-amine

Procedure

4-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)thiazol-2-amine was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine via General Procedure B to give, after purification by reverse HPLC, 41 mg of 429. MS (Q1) 436 (M+)

Workup

  1. customto give
  2. customafter purification by reverse HPLC, 41 mg of 429

Sources & evidence

ORD record
ord-e70d4734f18a4a5b812a9512f0d0873e
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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