Triethylamine → HCID 178429489, compound

HRID 576966Notes

Reaction equation

HRID 576966 reaction equation
Br[CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[Cl:13])=[CH:10][CH:9]=[CH:8][CH:7]=2.[CH3:14][C:15]1[N:20]=[C:19]([SH:21])[N:18]=[C:17]([OH:22])[CH:16]=1.C(N(CC)CC)C>C(O)C>[ClH:13].[Cl:13][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:2][S:21][C:19]1[N:18]=[C:17]([OH:22])[CH:16]=[C:15]([CH3:14])[N:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59589356HCID 59589356, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429489HCID 178429489, compoundYield 141.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(bromomethyl)-4-chloroquinoline (982 mg, 3.8 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (450 mg, 3.2 mmol), and triethylamine (1.3 mL, 9.5 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The solvent was evaporated to dryness and co-evaporated with EtOAc (20 mL). The product was suspended in water (200 mL). The product was recovered by filtration and washed with water (3×200 mL), diethyl ether (1×50 mL), and hexanes (2×50 mL). The solid material was dried in vacuo, affording the title compound (951 mg, 79% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 4.65 (s, 2H), 6.02 (s (br), 1H), 7.75 (td, 1H, J=1.4 Hz, 6.8 Hz), 7.83 (td, 1H, J=1.4 Hz, 6.8 Hz), 8.05 (dd, 1H, J=0.6 Hz, 7.6 Hz), 8.20 (dd, 1H, J=0.6 Hz, 8.4 Hz), 9.10 (s, 1H); M+ 318.

Workup

  1. customThe solvent was evaporated to dryness and co-evaporated with EtOAc (20 mL)
  2. filtrationThe product was recovered by filtration
  3. washwashed with water (3×200 mL), diethyl ether (1×50 mL), and hexanes (2×50 mL)
  4. customThe solid material was dried in vacuo

Sources & evidence

ORD record
ord-68d5cecb92884983b0a8f4616db4f726
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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