Diisopropylethylamine → (S)-2-Amino-4-((1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-6-methylpyrimidine-5-carbonitrile

HRID 2205628Notes

Reaction equation

HRID 2205628 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:13]([CH3:14])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C@@H:8]([NH2:10])[CH3:9].[NH2:15][C:16]1[N:21]=[C:20](Cl)[C:19]([C:23]#[N:24])=[C:18]([CH3:25])[N:17]=1.CCN(C(C)C)C(C)C>C(#N)C>[NH2:15][C:16]1[N:21]=[C:20]([NH:10][C@H:8]([C:7]2[N:6]=[C:5]3[CH:11]=[CH:12][N:13]([CH3:14])[C:4]3=[CH:3][C:2]=2[Br:1])[CH3:9])[C:19]([C:23]#[N:24])=[C:18]([CH3:25])[N:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 754124462-Amino-4-chloro-6-methyl-5-pyrimidinecarbonitrileHCID 86707977(S)-1-(6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

Product 1

HCID 118207725(S)-2-Amino-4-((1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-6-methylpyrimidine-5-carbonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A microwave vial was charged with (S)-1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine (2 g, 7.87 mmol), 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (1.592 g, 9.44 mmol), acetonitrile (40 mL), and DIPEA (5.50 mL, 31.5 mmol). The reaction mixture was heated to 75° C. for 1 hour in an oil bath and then cooled to room temperature. A precipitate was isolated by vacuum filtration and washed with acetonitrile to give the title compound as an off-white solid (2.85 g, 94%). ESI-MS m/z [M+H]+ calc'd for C16H16BrN7, 386. found 386.

Workup

  1. temperaturecooled to room temperature
  2. customA precipitate was isolated by vacuum filtration
  3. washwashed with acetonitrile

Sources & evidence

ORD record
ord-51459d3cb97d4a58aaf30465df765fdc
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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