Triethylamine → 6-methyl-2-[(4-propan-2-yl-1,3-thiazol-5-yl)methylsulfanyl]-1H-pyrimidin-4-one

HRID 577095Notes

Reaction equation

HRID 577095 reaction equation
Br[CH2:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[CH:8]([CH3:10])[CH3:9].[CH3:11][C:12]1[N:17]=[C:16]([SH:18])[N:15]=[C:14]([OH:19])[CH:13]=1.C(N(CC)CC)C>C(O)C>[CH3:11][C:12]1[N:17]=[C:16]([S:18][CH2:2][C:3]2[S:7][CH:6]=[N:5][C:4]=2[CH:8]([CH3:10])[CH3:9])[N:15]=[C:14]([OH:19])[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 595893685-(Bromomethyl)-4-(propan-2-yl)-1,3-thiazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 1784295326-methyl-2-[(4-propan-2-yl-1,3-thiazol-5-yl)methylsulfanyl]-1H-pyrimidin-4-oneYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(bromomethyl)-4-(propan-2-yl)-1,3-thiazole (5.1 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (510 mg, 3.6 mmol), and triethylamine (2.2 mL, 15.8 mmol) in absolute ethanol (30 mL) was stirred at room temperature overnight. The mixture was evaporated to dryness and then co-evaporated with EtOAc (20 mL). The residue was treated with water (100 mL). The solid material was recovered by filtration and washed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL). The solid material was dried in vacuo, affording the title compound (565 mg, 56% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.20 (d, 6H, J=6.8 Hz), 2.24 (s, 3H), 3.27 (m, 1H), 4.61 (s, 2H), 6.03 (s, 1H), 8.84 (s, 1H); M+ 282.

Workup

  1. customThe mixture was evaporated to dryness
  2. additionThe residue was treated with water (100 mL)
  3. filtrationThe solid material was recovered by filtration
  4. washwashed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL)
  5. customThe solid material was dried in vacuo

Sources & evidence

ORD record
ord-b8b23e5e198b490ea93c443c9d2eafa0
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…