(3-Amino-4-methylphenyl)boronic acid → HCID 66617799, compound

HRID 2403432Notes

Reaction equation

HRID 2403432 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.[NH2:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[CH3:32]>>[CH3:32][C:31]1[CH:30]=[CH:29][C:28]([C:2]2[N:3]=[C:4]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:5]3[S:10][C:9]([CH2:11][N:12]4[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]4)=[CH:8][C:6]=3[N:7]=2)=[CH:27][C:26]=1[NH2:25]

Participants

3

Reactant 2

HCID 2737803(3-Amino-4-methylphenyl)boronic acidHCID 574203384-(2-Chloro-6-((4-methylpiperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 66617799HCID 66617799, compound

Procedure

2-Chloro-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine was reacted with 3-amino-4-methylbenzeneboronic acid in general procedure A. Purification by flash chromatography on silica yielded 2-Methyl-5-[6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl]-phenylamine. To a solution of 2-Methyl-5-[6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl]-phenylamine (154 mg) in chloroform (10 ml) and acetic acid (2 ml) was added isoamyl nitrite (55 μL). The reaction mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with chloroform and washed with a 50/50 mixture of saturated sodium bicarbonate solution and brine, dried (MgSO4) and the solvents were removed in vacuo to give a crude residue. This was purified by flash chromatography to yield the desired product.

Workup

  1. customPurification by flash chromatography on silica

Sources & evidence

ORD record
ord-f633efa634b64cc6baa56c762f3f3172
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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