Triethylamine → HCID 178428298, compound

HRID 229329Notes

Reaction equation

HRID 229329 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[N:5]=[C:4](/[CH:12]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.C(N(CC)CC)C.[NH2:27][C:28]1[CH:32]=[C:31]([CH3:33])[NH:30][N:29]=1.[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C1COCC1.C(OCC)(=O)C.O>[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([C:6]2[N:5]=[C:4](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:3]=[C:2]([NH:27][C:28]3[NH:29][N:30]=[C:31]([CH3:33])[CH:32]=3)[C:7]=2[N+:8]([O-:10])=[O:9])[CH2:37][CH2:36]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 46705555HCID 46705555, compound

Product 1

HCID 178428298HCID 178428298, compoundYield 28.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,6-dichloro-5-nitro-2-[(E)-2-phenylvinyl]pyrimidine (200 mg, 0.676 mmol) in THF (5 mL) was added triethylamine (204 mg, 2.03 mmol) and the reaction mixture was stirred for 15 minutes. 3-Amino-5-methyl-pyrazole (66 mg, 0.68 mmol) in THF (3 mL) was added dropwise to the reaction mixture. After 1 hour, N-methylpiperazine (74 mg, 0.74 mmol) in THF (3 mL) was added to the reaction mixture dropwise. The reaction mixture was stirred at room temperature for 1 hour followed by addition of water (10 mL). After stirring for 15 minutes, ethyl acetate (50 mL) was added. The organic layer was separated, dried and the solvent evaporated under reduced pressure. The residue was triturated with chloroform and hexane to obtain 6-(4-methylpiperazin-1-yl)-N-(3-methyl- 1H-pyrazol-5-yl)-5-nitro-2-[(E)-2-phenylvinyl]pyrimidin-4-amine (80 mg). 1H NMR (400 MHz, DMSO-d6): δ 12.35 (br, 1H), 10.52 (br, 1H), 7.95 (d, 1H, J=16 Hz), 7.83 (d, 2H, J=6.8 Hz), 7.5 (m, 3H), 7.11 (d, 1H, J=16 Hz), 6.8 (s, 1H), 3.65 (br, 4H), 2.5 (br, 4H), 2.36 (s, 3H), 2.29 (s, 3H). MS (m/z) 421 (M+1).

Workup

  1. waitAfter 1 hour
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. stirringAfter stirring for 15 minutes
  4. customThe organic layer was separated
  5. customdried
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was triturated with chloroform and hexane

Sources & evidence

ORD record
ord-60788926f33f4d7dbdf4c4a087f6c7fc
Source dataset
uspto-grants-2009_07
Patent number
US07563787B2

Reaction notes

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