4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 46180663, compound

HRID 2403365Notes

Reaction equation

HRID 2403365 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:36]2[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=2)O1>>[CH3:21][S:18]([N:15]1[CH2:16][CH2:17][N:12]([CH2:11][C:9]2[S:10][C:5]3[C:4]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[N:3][C:2]([C:36]4[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=4)=[N:7][C:6]=3[CH:8]=2)[CH2:13][CH2:14]1)(=[O:20])=[O:19]

Participants

3

Reactant 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 236508374-(2-Chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 46180663HCID 46180663, compound

Procedure

2-Chloro-6-(4-methylsulfonyl-piperazine-1-yl-methyl)-4-morpholin-4-yl-thieno[3,2-d}pyrimidine was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline in General Procedure A. Purification on silica yielded 4-[6-(4-Methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl]-aniline. This was then reacted with acetic anhydride in dichloromethane and triethylamine to give the desired compound.

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-6cf5f35eafac45b185cc2ea2e67b0eb6
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

Loading…