Triethylamine → HCID 178462659, compound

HRID 577032Notes

Reaction equation

HRID 577032 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH3:16])[CH2:11][CH2:10]2)=[CH:5][C:4]=1[Cl:17].[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:17][C:4]1[CH:5]=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH3:16])[CH2:11][CH2:10]2)[CH:7]=[CH:8][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 595894741-[4-(Bromomethyl)-3-chlorophenyl]-4-ethylpiperazineHCID 178429541HCID 178429541, compound

Product 1

HCID 178462659HCID 178462659, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[4-(bromomethyl)-3-chlorophenyl]-4-ethylpiperazine, 6-methyl-2-sulfanylpyrimidin-4-ol (1.42 g, 10 mmol) and triethylamine (2.8 mL, 20 mmol) were mixed in ethanol (50 mL). The mixture was stirred at room temperature for 2 hours. After evaporation, water (100 mL) was added. The suspension was filtered and washed with water and ethyl acetate to provide crude product, which was further purified by CombiFlash to yield a white solid (400 mg, 5% overall yield); 1H NMR (400 MHz, DMSO-d6): δ 1.16 (t, 3H), 2.20 (s, 3H), 2.48 (q, 4H), 3.06 (q, 4H), 4.35 (s, 2H), 5.98 (br, 1H), 6.88 (d, 1H), 7.00 (s, 1H), 7.42 (d, 1H); M+ 379.

Workup

  1. customAfter evaporation, water (100 mL)
  2. additionwas added
  3. filtrationThe suspension was filtered
  4. washwashed with water and ethyl acetate
  5. customto provide crude product, which
  6. customwas further purified by CombiFlash
  7. customto yield
  8. customa white solid (400 mg, 5% overall yield)

Sources & evidence

ORD record
ord-7d84d0a1690d49ec806adcdafda70094
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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