Diisopropylethylamine → Ethyl 4-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-chloropyrimidine-5-carboxylate

HRID 1802017Notes

Reaction equation

HRID 1802017 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[N:23]1([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[CH:27]=[N:26][CH:25]=[N:24]1>CC#N.O>[N:23]1([C:28]2[CH:29]=[CH:30][C:31]([NH:32][C:6]3[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)=[CH:33][CH:34]=2)[CH:27]=[N:26][CH:25]=[N:24]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylateHCID 7358264-(1,2,4-Triazol-1-yl)aniline

Product 1

HCID 57471895Ethyl 4-(4-(1H-1,2,4-triazol-1-yl)phenylamino)-2-chloropyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 2,4-dichloropyrimidine-5-carboxylate (1.4) (600 mg, 2.714 mmol), in CH3CN (12 mL), was added DIEA (0.750 mL, 4.313 mmol, 1.589 equiv), followed by 4-(1H-1,2,4-triazol-1-yl)aniline (465 mg, 2.902 mmol, 1.07 equiv). The mixture was stirred at room temperature for 20 h, then diluted with water (6×) to precipitate ii. The solid product was collected by filtration, rinsed with water (100 mL), and air dried; Yield, 850 mg (91%).

Workup

  1. customto precipitate ii
  2. filtrationThe solid product was collected by filtration
  3. washrinsed with water (100 mL), and air
  4. customdried
  5. customYield

Sources & evidence

ORD record
ord-72e2441b0235467b8ef5524c2d922181
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Reaction notes

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