Triethylamine → 2-[(3-chloro-1-benzothiophen-2-yl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

HRID 576937Notes

Reaction equation

HRID 576937 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(N(CC)CC)C.Br[CH2:18][C:19]1[S:20][C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[C:23]=1[Cl:24]>C(O)C>[Cl:24][C:23]1[C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[S:20][C:19]=1[CH2:18][S:8][C:6]1[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8167082-(Bromomethyl)-3-chloro-1-benzothiopheneHCID 178429541HCID 178429541, compound

Product 1

HCID 1784295302-[(3-chloro-1-benzothiophen-2-yl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 60.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (148 mg, 1.0 mmol) was dissolved in absolute ethanol (8 mL), then triethylamine (180 μL, 1.3 mmol) and 2-(bromomethyl)-3-chloro-1-benzothiophene (300 mg, 1.2 mmol) were added. The mixture was stirred overnight at room temperature. The precipitate was filtered, washed with ethanol and water and then diethyl ether, and dried in vacuo to afford to 2-{[(3-chloro-1-benzothiophen-2-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (195 mg, 58% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.27 (s, 3H), 4.72 (s, 2H), 5.69 (s, 1H), 6.07 (bs, 1H), 7.43-7.53 (m, 2H), 7.73-7.76 (m, 1H), 7.97-8.00 (m, 114), 12.29 (bs, 1H); LRMS (ES+) m/z 323 (100%, M+1), 325 (35%, M+3).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ethanol and water
  3. dry with materialdiethyl ether, and dried in vacuo

Sources & evidence

ORD record
ord-88a484b6ba174255a29375ac2cf69202
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…