1-Ethylpiperazine → HCID 178462660, compound

HRID 630248Notes

Reaction equation

HRID 630248 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-98ee9b73fbf44c9b9e52652295e99a86
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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