Triethylamine → HCID 178429469, compound

HRID 576973Notes

Reaction equation

HRID 576973 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[F:25]>C(O)C>[F: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 574754504-(Bromomethyl)-3-fluoropyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429469HCID 178429469, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-methyl-2-sulfanylpyrimidin-4-ol (152 mg, 1.1 mmol) was dissolved in absolute ethanol (20 mL), then triethylamine (200 μL, 1.4 mmol) and 4-(bromomethyl)-3-fluoropyridine (260 mg, 1.4 mmol) were added. The mixture was stirred over the weekend at room temperature. The solid was removed by filtration and washed with methanol. The filtrate was evaporated, and the residue was triturated in methanol, filtered, washed with water and diethyl ether, and then dried in vacuo to afford to 2-{[(3-fluoropyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (14 mg, 7% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.18 (s, 3H), 4.41 (s, 2H), 6.00 (bs, 1H), 7.58 (t, J=5.7 Hz, 1H), 8.37 (dd, J=0.8 Hz, J=4.9 Hz, 1H), 8.53 (d, J=1.8 Hz, 1H); LRMS (ES+) m/z 252 (100%, M+1).

Workup

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

Sources & evidence

ORD record
ord-f966255c858847039e04f6750fbad777
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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