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Diisopropylethylamine → N-{5-chloro-2-{[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methoxy-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N-methylmethanesulfonamide

HRID 415405
Notes
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Reaction equation

HRID 415405 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([Cl:14])=[C:4]([NH:15][C:16]2[CH:20]=[C:19]([O:21][CH3:22])[NH:18][N:17]=2)[N:3]=1.Cl.[F:24][C:25]1[CH:26]=[N:27][C:28]([C@@H:31]([NH2:33])[CH3:32])=[N:29][CH:30]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:14][C:5]1[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[N:7][C:2]([NH:33][C@H:31]([C:28]2[N:29]=[CH:30][C:25]([F:24])=[CH:26][N:27]=2)[CH3:32])=[N:3][C:4]=1[NH:15][C:16]1[CH:20]=[C:19]([O:21][CH3:22])[NH:18][N:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66624037(S)-1-(5-Fluoropyrimidin-2-yl)ethanamine hydrochlorideHCID 178493076N-{2,5-dichloro-6-[(5-methoxy-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N-methylmethanesulfonamide

Product 1

HCID 178493098N-{5-chloro-2-{[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methoxy-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N-methylmethanesulfonamideYield 77%

Reagents, catalysts & solvents

1
HCID 2631-ButanolSolvent

Conditions

Temperature
160 °C

Procedure

A microwave reaction vessel was charged with N-{2,5-dichloro-6-[(5-methoxy-1H-pyrazol-3-yl)amino]pyrimidin-4-yl}-N-methylmethanesulfonamide (Method 25, 63.8 mg, 0.174 mmol), (S)-1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (Method 7, 61.7 mg, 0.348 mmol), and DIPEA (0.122 ml, 0.693 mmol). Anhydrous n-BuOH (1 ml) was added, and the tube was sealed and heated in a microwave reactor at 160° C. for 2 hours. The reaction mixture was purified by silica gel chromatography (by ISCO Combiflash with gradient EtOAc and hexane) to afford the title compound as a white solid (63.1 mg, 77%). LC-MS: 472 (M+1). 1H NMR (DMSO-d6, 400 MHz) δ 11.71 (s, 1H), 9.40 (s, 1H), 8.77 (s, 2H), 7.91 (s, 1H), 5.65 (s, 1H), 5.07-5.10 (m, 1H), 3.79 (s, 3H), 3.01 (s, 6H), 1.54 (d, 3H).

Workup

  1. customA microwave reaction vessel
  2. customthe tube was sealed
  3. customThe reaction mixture was purified by silica gel chromatography (by ISCO Combiflash with gradient EtOAc and hexane)

Sources & evidence

ORD record
ord-f08b403f03cb429dafbe86afdb862a87
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08088784B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes