Ethanethiol → 3-hydroxy-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one

HRID 625954Notes

Reaction equation

HRID 625954 reaction equation
C([O:8][C:9]1[C:10](=[O:28])[N:11]([CH3:27])[CH:12]=[C:13]([C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:17][N:16]=2)[CH:14]=1)C1C=CC=CC=1.C(S)C.B(F)(F)F.CCOCC>CO>[OH:8][C:9]1[C:10](=[O:28])[N:11]([CH3:27])[CH:12]=[C:13]([C:15]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][N:16]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 674194493-(benzyloxy)-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one

Product 1

HCID 533799013-hydroxy-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-oneYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(benzyloxy)-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one (21 mg, 0.057 mmol) was added ethanethiol (31.8 mg, 0.512 mmol) followed by BF3.OEt2 (73 mg, 0.512 mmol). The resulting solution was stirred at room temperature for 18 h, diluted with MeOH and concentrated. Purification by preparative HPLC (5-50% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 7.3 mg 3-hydroxy-1-methyl-5-(4-phenylpyrimidin-2-yl)pyridin-2(1H)-one (46%) as a light purple solid. 1H NMR (500 MHz, DMSO-d6): δ 9.41 (br s, 1H), 8.84 (d, J=5.3 Hz, 1H); 8.44 (s, 1H); 8.33 (s, 2 H); 7.90 (d, J=5.3 Hz, 1H); 7.72 (s, 1H); 7.59 (s, 3H); 3.65 (s, 3H). High resolution mass spec (FT/ICR) calc (M+H)+=280.1081 found 280.1080.

Workup

  1. concentrationconcentrated
  2. customPurification
  3. additionby preparative HPLC (5-50% CH3CN/H2O over 20 min, 0.05% added TFA)

Sources & evidence

ORD record
ord-44cc42d15a9b4df9b82838e8a8b4b5b2
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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