2-Mercaptoethanol → N-(4-Fluorophenyl)-2-[(2-hydroxyethyl)sulfanyl]pyrimidine-5-carboxamide

HRID 348436Notes

Reaction equation

HRID 348436 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([S:17]([CH3:19])=O)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.SC[CH2:22][OH:23].C1CCN2C(=NCCC2)CC1.ClCCl.CCCCCC>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([S:17][CH2:19][CH2:22][OH:23])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21226440Methylenechloride HexaneHCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 71423463N-(4-Fluorophenyl)-2-[(2-hydroxyethyl)sulfanyl]pyrimidine-5-carboxamideYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (39 mg, 0.14 mmol) in THF (1 mL) was added β-mercaptoethanol (20 μL, 0.28 mmol) followed by DBU (43 μL, 0.28 mmol). After 15 min the reaction was quenched with 40 mL 1% HCl, resulting in the formation of solids. The solids were collected by filtration and washed with water. The filtrate was extracted with dichloromethane to afford a white solid after concentration. These were combined with the solids isolated from the filtration and passed through a plug of SiO2 using 60% ethyl acetate/hexane to afford a white solid. After trituration with dichloromethane/hexane, 19.3 mg (47% yield) of titled product was obtained. API-MS m/z 294 (MH+), 292 (M−H)−.

Workup

  1. customAfter 15 min the reaction was quenched with 40 mL 1% HCl
  2. customresulting in the formation of solids
  3. filtrationThe solids were collected by filtration
  4. washwashed with water
  5. extractionThe filtrate was extracted with dichloromethane
  6. customto afford a white solid
  7. concentrationafter concentration
  8. customisolated from the filtration
  9. customto afford a white solid

Sources & evidence

ORD record
ord-3d829e56b6c1430dbd316e4b7884cf56
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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