Diisopropylethylamine → 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyrimidin-2-ylmethyl)pyrimidin e-5-carboxamide

HRID 874509Notes

Reaction equation

HRID 874509 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.CCN(C(C)C)C(C)C.CN(C(O[N:40]1N=[N:47][C:42]2[CH:43]=[CH:44][CH:45]=[N:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C=CC=NC=1CN>C1COCC1.O>[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]([NH:47][CH2:42][C:41]2[N:40]=[CH:43][CH:44]=[CH:45][N:46]=2)=[O:15])=[CH:11][N:10]=[C:9]([S:16][CH3:17])[N:8]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 46580472-PyrimidinemethanamineHCID 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 712350354-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyrimidin-2-ylmethyl)pyrimidin e-5-carboxamideYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic acid (300 mg, 0.88 mmol), DIEA (0.5 mL, 2.88 mmol) were dissolved in 30 mL of THF, HATU (405 mg, 1.06 mmol) and pyrimidin-2-ylmethylamine (115 mg, 1.06 mmol) were added under ice-water-bath, reacted at room temperature overnight, to the reaction solution was added 100 mL of water, then extracted with dichloromethane, dried with anhydrous sodium sulfate, dried by rotation, then solid was separated with silica gel column (dichloromethane:methanol=40:1) to obtain a white solid 4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide 60 mg, yield 16%.

Workup

  1. customreacted at room temperature overnight, to the reaction solution
  2. extractionextracted with dichloromethane
  3. dry with materialdried with anhydrous sodium sulfate
  4. customdried by rotation
  5. customsolid was separated with silica gel column (dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-7dcf218bcd5b4ae48a246240ce0e5301
Source dataset
uspto-grants-2015_03
Patent number
US08980904B2

Reaction notes

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