Triethylamine → 3-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-N-methoxy-4,N-dimethyl-benzamide

HRID 2172604Notes

Reaction equation

HRID 2172604 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:12](O)=[O:13])[C:5]([CH3:19])=[N:4][C:3]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=1.[C:29](N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:42][N:43](C)[OH:44].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:12]([N:43]([O:44][CH3:29])[CH3:42])=[O:13])[C:5]([CH3:19])=[N:4][C:3]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 866862903-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid

Product 1

HCID 715826473-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-N-methoxy-4,N-dimethyl-benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid from Step C (220 mg, 0.56 mmol) in tetrahydrofuran (2 mL) was added 1,1′-carbonyldiimidazole (136 mg, 0.84 mmol). After stirring at ambient temperature for one hour, N,N-dimethylhydroxylamine HCl (81 mg, 0.84 mmol) and triethylamine (0.15 mL, 1.12 mmol) were added. The solution continued to stir for eighteen hours. The solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium bicarbonate, water, 5% citric acid and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the amide as a brown oil (193 mg, 78%). MS (M+H): 442

Workup

  1. stirringto stir for eighteen hours
  2. customThe solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated sodium bicarbonate, water, 5% citric acid and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-11b691c0c3ed42b29e96e483e654045a
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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