Triethylamine → HCID 178429511, compound

HRID 630044Notes

Reaction equation

HRID 630044 reaction equation
Br[CH2:2][C:3]1[S:7][CH:6]=[N:5][CH:4]=1.[CH3:8][C:9]1[N:14]=[C:13]([SH:15])[N:12]=[C:11]([OH:16])[CH:10]=1.C(N(CC)CC)C>C(O)C>[CH3:8][C:9]1[N:14]=[C:13]([S:15][CH2:2][C:3]2[S:7][CH:6]=[N:5][CH:4]=2)[N:12]=[C:11]([OH:16])[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 216984015-(Bromomethyl)-1,3-thiazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178429511HCID 178429511, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(bromomethyl)-1,3-thiazole (4.3 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (427 mg, 3.0 mmol), and triethylamine (1.7 mL, 12.0 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The mixture was evaporated and then co-evaporated with EtOAc (20 mL). The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL), and then dried in vacuo. The crude product was purified by flash chromatography (0-5% MeOH/CH2Cl2), affording the title compound (28 mg, 4% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.09 (s, 3H), 4.64 (s, 2H), 4.16 (s, 2H), 6.02 (s (br), 1H), 7.87 (d, 1H, J=0.8 Hz), 8.94 (s, 1H); M+240.

Workup

  1. customThe mixture was evaporated
  2. additionThe solid residue was treated with water (100 mL)
  3. filtrationThe solid product was recovered by filtration
  4. washwashed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL)
  5. customdried in vacuo
  6. customThe crude product was purified by flash chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-82e575e39f1a42449776a91f46e17bfc
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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