Sodium Hydroxide → 5-(4-(Ethylsulfonyl)piperazin-1-yl)-3-(6-phenylpyrimidin-4-yl)pyrazin-2-amine
Reaction equation
[NH2:1][C:2]1[C:3]([C:19](=O)[CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.Cl.[CH:30]([NH2:32])=[NH:31].[OH-].[Na+]>>[CH2:17]([S:14]([N:11]1[CH2:12][CH2:13][N:8]([C:5]2[N:4]=[C:3]([C:19]3[CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:32]=[CH:30][N:31]=3)[C:2]([NH2:1])=[N:7][CH:6]=2)[CH2:9][CH2:10]1)(=[O:16])=[O:15])[CH3:18]Participants
Procedure
A mixture of 1-(3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)pyrazin-2-yl)-3-phenylprop-2-en-1-one (45 mg, 0.1121 mmol), formamidine hydrochloride (9.026 mg, 0.1121 mmol) and NaOH (4.932 mg, 0.1233 mmol) were heated at reflux for 1 hour. The reaction mixture was allowed to cool to ambient temperature and the solvent removed in vacuo. The resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B, (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (73 mg, 4% Yield). 1H NMR (400.0 MHz, DMSO) d 1.25 (t, 3H), 3.12 (q, 2H), 3.36-3.38 (m, 4H), 3.56-3.59 (m, 4H), 7.15 (br s, 2H), 7.60-7.61 (m, 3H), 8.25-8.26 (m, 3H), 8.76 (s, 1H) and 9.31 (s, 1H) ppm; MS (ES+) 426.0
Workup
- temperaturewere heated
- temperatureat reflux for 1 hour
- customthe solvent removed in vacuo
- customThe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B, (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
- customThe fractions were collected
- customfreeze-dried
Sources & evidence
- ORD record
- ord-30ae8411a13d4f509e823dd2ca4aad0b
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410112B2
Reaction notes
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