Triethylamine → HCID 178462652, compound

HRID 576990Notes

Reaction equation

HRID 576990 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH3:17])[CH2:12][CH2:11]1.[CH3:18][C:19]1[N:24]=[C:23]([SH:25])[N:22]=[C:21]([OH:26])[CH:20]=1.C(N(CC)CC)C>C(O)C>[Cl:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH3:17])[CH2:12][CH2:11]2)[C:3]=1[CH2:2][S:25][C:23]1[N:22]=[C:21]([OH:26])[CH:20]=[C:19]([CH3:18])[N:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59589447HCID 59589447, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178462652HCID 178462652, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[2-(bromomethyl)-3-chlorophenyl]-4-ethylpiperazine (24.8 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (2.35 g, 16.5 mmol), and triethylamine (17 mL, 124 mmol) in absolute ethanol (300 mL) was stirred at room temperature overnight. The solid material was removed by filtration. The filtrate was recovered and evaporated. The solid residue was treated with water (500 mL). The mixture was extracted with DCM (3×200 mL) and EtOAc (1×200 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-20% MeOH/DCM and 0-15% MeOH/DCM), affording 2-({[2-chloro-6-(4-ethylpiperazin-1-yl)phenyl]methyl}sulfanyl)-6-methylpyrimidin-4-ol (505 mg, 5% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.00 (t, 3H, J=7.2 Hz), 2.24 (s, 3H), 2.85 (m, 2H), 2.50 (m, 4H), 2.87 (m, 4H), 4.67 (s, 2H), 6.02 (s, 1H), 7.22 (m, 2H), 7.32 (t, 1H, J=8.0 Hz); M+ 379.

Workup

  1. customThe solid material was removed by filtration
  2. customThe filtrate was recovered
  3. customevaporated
  4. additionThe solid residue was treated with water (500 mL)
  5. extractionThe mixture was extracted with DCM (3×200 mL) and EtOAc (1×200 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customdried in vacuo
  10. customThe crude product was purified by flash chromatography (0-20% MeOH/DCM and 0-15% MeOH/DCM)

Sources & evidence

ORD record
ord-97b3f9b2a48346f2848945c31226e5fb
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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