Triethylamine → HCID 178462659, compound

HRID 630073Notes

Reaction equation

HRID 630073 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-799e50e5ce4c4598a692f27d2abc51b7
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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