Benzylamine → N-benzyl-4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxamide

HRID 874507Notes

Reaction equation

HRID 874507 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:5][O:6][C:7]1[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1.O>[CH2:23]([NH:30][C:13]([C:12]1[C:7]([O:6][CH2:5][C:4]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:2]([Cl:1])[CH:3]=2)=[N:8][C:9]([S:16][CH3:17])=[N:10][CH:11]=1)=[O:15])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712350394-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic Acid

Product 1

HCID 71235045N-benzyl-4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxamideYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic acid (2.2 g, 6.47 mmol), benzylamine (1.0 g, 9.34 mmol) and HATU (2.95 g, 7.76 mmol) were dissolved in 60 mL of THF, DIEA (N,N-diiso-propylethylamine, 3.36 mL, 19.41 mmol) was added dropwise, reacted at room temperature for 8 h. To the reaction solution was added 100 mL of water and then extracted with dichloromethane (50 mL×3), dried with anhydrous sodium sulfate, dried by rotation, the solid was separated with silica gel column (dichloromethane:methanol=100:1) to obtain a white solid N-benzyl-4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxamide 600 mg, 22% yield.

Workup

  1. customreacted at room temperature for 8 h
  2. extractionextracted with dichloromethane (50 mL×3)
  3. dry with materialdried with anhydrous sodium sulfate
  4. customdried by rotation
  5. customthe solid was separated with silica gel column (dichloromethane:methanol=100:1)

Sources & evidence

ORD record
ord-78133963d020484991ba3f03da85d106
Source dataset
uspto-grants-2015_03
Patent number
US08980904B2

Reaction notes

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