Triethylamine → HCID 178429467, compound

HRID 629991Notes

Reaction equation

HRID 629991 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[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[Cl:25]>C(O)C>[Cl:25][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][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 595894074-(Bromomethyl)-3-chloropyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429467HCID 178429467, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (242 mg, 1.7 mmol) was dissolved in absolute ethanol (10 mL), then triethylamine (350 μL, 2.5 mmol) and 4-(bromomethyl)-3-chloropyridine (350 mg, 1.7 mmol) in absolute ethanol (5 mL) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration, and the filtrate was evaporated. The residue was triturated in diethyl ether, filtered, washed with water plus diethyl ether, and then dried in vacuo to afford to 2-{[(3-chloropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (158 mg, 35% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.20 (s, 3H), 4.46 (s, 2H), 6.03 (bs, 1H), 7.63 (d, J=5.0 Hz, 1H), 8.47 (d, J=5.0 Hz, 1H), 8.63 (s, 1H); LRMS (ES+) m/z 268 (100%, M+1), 270 (65%, M+3).

Workup

  1. customThe solid was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was triturated in diethyl ether
  4. filtrationfiltered
  5. washwashed with water plus diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f8def3e5074d4a9e89a075ba61e96451
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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