Triethylamine → HCID 178429480, compound

HRID 630038Notes

Reaction equation

HRID 630038 reaction equation
Br[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][O:6][C:7]=1[CH3:8].[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1.C(N(CC)CC)C>C(O)C>[CH3:9][C:4]1[C:3]([CH2:2][S:17][C:15]2[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=2)=[C:7]([CH3:8])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127932894-(Bromomethyl)-3,5-dimethyl-1,2-oxazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178429480HCID 178429480, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromomethyl)-3,5-dimethyl-1,2-oxazole (6.3 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (611 mg, 4.3 mmol), and triethylamine (5 mL, 36.0 mmol) in absolute ethanol (25 mL) was stirred at room temperature overnight. The solid material was removed by filtration. The filtrate was recovered, evaporated, and co-evaporated with EtOAc (20 mL). The solid residue was treated with water (200 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, affording the title compound (783 mg, 72% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.19 (m, 6H), 2.40 (s, 3H), 4.16 (s, 2H), 5.99 (s (br), 1H); M+252.

Workup

  1. customThe solid material was removed by filtration
  2. customThe filtrate was recovered
  3. customevaporated
  4. additionThe solid residue was treated with water (200 mL)
  5. filtrationThe solid product was recovered by filtration
  6. washwashed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-12b942ff5a554cbcb59d4e5b67da7e27
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…