Triethylamine → HCID 11948303, compound

HRID 221959Notes

Reaction equation

HRID 221959 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=3)[C:8]2=[O:24])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].C([O-])(O)=O.[Na+]>O.C1COCC1>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:9]2[CH2:10][CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:26][CH:25]=3)[C:8]2=[O:24])=[CH:15][CH:16]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 59707078HCID 59707078, compound

Product 1

HCID 11948303HCID 11948303, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-tetrahydropyrimidin-2-one (L) (438 mg, 1.24 mmol) and triethylamine (0.22 mL, 1.6 mmol) in abs. THF (50 mL) there was added a solution of methanesulphonyl chloride (0.11 mL, 1.48 mmol) in 5 mL of abs. THF within a period of 15 min. The reaction mixture was stirred over a period of 48 h at RT, sat. NaHCO3 solution (20 mL) was added, and the mixture was stirred for 30 min. H2O (30 mL) was added, and the mixture was extracted with EtOAc (3×30 mL). The combined organic phases were washed with sat. NaCl solution (30 mL), dried over Na2SO4, and the solvent was removed in vacuo. The residue was purified by means of column chromatography (SiO2 (50 g) using cyclohexane/EtOAc 1:1 (500 mL) as eluent). The desired product N-{4-[3-(4-tert-butyl benzyl)-2-oxotetrahydropyrimidin-1-yl methyl]phenyl}methanesulfonamide (5) was obtained as a white solid (398 mg, 75% of theory) having a melting point of 132-135° C.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. extractionthe mixture was extracted with EtOAc (3×30 mL)
  3. washThe combined organic phases were washed with sat. NaCl solution (30 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by means of column chromatography (SiO2 (50 g) using cyclohexane/EtOAc 1:1 (500 mL) as eluent)

Sources & evidence

ORD record
ord-9b3f9152018845cb8d96d43f6e159b2c
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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