1-Ethylpiperazine → HCID 178462660, compound

HRID 577206Notes

Reaction equation

HRID 577206 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[CH:6][CH:5]=[C:4]([Cl:18])[N:3]=1.[CH2:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[CH3:20]>CS(C)=O>[Cl:1][C:2]1[C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[CH:6][CH:5]=[C:4]([N:24]2[CH2:25][CH2:26][N:21]([CH2:19][CH3:20])[CH2:22][CH2:23]2)[N:3]=1.[Cl:18][C:4]1[N:3]=[C:2]([N:24]2[CH2:25][CH2:26][N:21]([CH2:19][CH3:20])[CH2:22][CH2:23]2)[C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([CH3:17])[N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 791961-EthylpiperazineHCID 1784294332-[(2,6-dichloro-3-pyridinyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

Product 2

HCID 178462660HCID 178462660, compoundHCID 178462713HCID 178462713, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-{[(2,6-dichloropyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (2.0 g, 6.61 mmol) and 1-ethylpiperazine (3.77 g, 26.88 mmol) was heated in DMSO (20 mL) at 90° C. overnight. After cooling, the mixture was extracted with ethyl acetate (2×100 mL). The organic layer was separated and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated to dryness and purified by CombiFlash chromatography using 0-20% dichloromethane:methanol to provide 2-({[2-chloro-6-(4-ethylpiperazin-1-yl)pyridin-3-yl]methyl}sulfanyl)-6-methylpyrimidin-4-ol (1H NMR (400 MHz, DMSO-d6): δ 1.02 (t, 3H), 2.18 (s, 3H), 2.31 (q, 2H), 2.56 (m, 4H), 3.42 (m, 4H), 4.30 (s, 2H), 6.01 (bs, 1H), 6.78 (d, J=8.4 Hz, 1H), 7.72 (d, J=8.4 Hz, 1H), LRMS (ES+) m/z 379.8) and 2-({[6-chloro-2-(4-ethylpiperazin-1-yl)pyridin-3-yl]methyl}sulfanyl)-6-methylpyrimidin-4-ol (1H NMR (400 MHz, DMSO-d6): δ 0.99 (t, 3H), 2.21 (s, 3H), 2.31 (q, 2H), 2.56 (m, 4H), 3.42 (m, 4H), 4.37 (s, 2H), 6.01 (bs, 1H), 7.06 (d, J=7.7 Hz, 1H), 7.77 (d, J=7.7 Hz, 1H), LRMS (ES+) m/z 379.8) as a white solid (1.73 g, 3:1 ratio, 69% yield).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. custompurified by CombiFlash chromatography

Sources & evidence

ORD record
ord-e401149118c74f54887a845e71492c13
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…