Diisopropylethylamine → 4-(2,4-Dimethoxybenzylamino)-3-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)benzonitrile

HRID 605864Notes

Reaction equation

HRID 605864 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:16]1[N:21]=[C:20](SC#N)[C:19]([N+:25]([O-:27])=[O:26])=[CH:18][N:17]=1.[NH2:34][CH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C(N(CC)C(C)C)(C)C>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:16]1[N:21]=[C:20]([NH:34][CH:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[C:19]([N+:25]([O-:27])=[O:26])=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 566052112-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanate

Product 1

HCID 597050054-(2,4-Dimethoxybenzylamino)-3-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)benzonitrileYield 98.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the suspension of 0.92 g (2.0 mmol) of 4-(2,4-dimethoxybenzylamino)-3-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)benzonitrile in 40 mL anhydrous THF was added 0.22 g (2.2 mmol) 4-amino-tetrahydropyran, then 0.7 mL (4.0 mmol) N,N-diisopropylethylamine. The mixture was stirred at room temperature under Argon balloon for 16 hrs till HPLC showed the completion of reaction. The mixture became clear then. The orange-red solution was diluted with EtOAc, washed with brine twice, and then dried over Na2SO4. Solvents were removed under vacuum to give 1.0 g orange-yellow solid as the crude product.

Workup

  1. customthe completion of reaction
  2. washwashed with brine twice
  3. dry with materialdried over Na2SO4
  4. customSolvents were removed under vacuum

Sources & evidence

ORD record
ord-5a2859aca78349d58b30ecb3ff309dcb
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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