Benzenemethanamine, 3,4-dimethyl- → 2-Amino-4-(4,5-dihydro-furan-2-yl)-6-(3,4-dimethyl-benzylamino)-pyrimidine-5-carbonitrile

HRID 1356123Notes

Reaction equation

HRID 1356123 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[C:5]([C:16]#[N:17])=[C:4]([C:18]2[O:19][CH2:20][CH2:21][CH:22]=2)[N:3]=1.[CH3:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[CH3:32])[CH2:27][NH2:28]>COCCOC>[NH2:1][C:2]1[N:3]=[C:4]([C:18]2[O:19][CH2:20][CH2:21][CH:22]=2)[C:5]([C:16]#[N:17])=[C:6]([NH:28][CH2:27][C:26]2[CH:29]=[CH:30][C:31]([CH3:32])=[C:24]([CH3:23])[CH:25]=2)[N:7]=1

Participants

4

Reactant 2

HCID 66888Benzenemethanamine, 3,4-dimethyl-HCID 86583757Trifluoromethanesulfonic acid 2-amino-5-cyano-6-(4,5-dihydro-furan-2-yl)-pyrimidin-4-yl ester

Product 1

HCID 185073622-Amino-4-(4,5-dihydro-furan-2-yl)-6-(3,4-dimethyl-benzylamino)-pyrimidine-5-carbonitrileYield 15%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of 250 mg (0.74 mmol) trifluoromethanesulfonic acid 2-amino-5-cyano-6-(4,5-dihydro-furan-2-yl)-pyrimidin-4-yl ester in 10 ml DME was added 0.20 g (1.49 mmol) 3,4-dimethylbenzylamine and the mixture stirred at room temperature for 1 hour. The reaction mixture was then partitioned between water and ethyl acetate and the organic phase was dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) followed by trituration in ether/hexane afforded 35 mg (15%) 2-amino-4-(4,5-dihydro-furan-2-yl)-6-(3,4-dimethyl-benzylamino)-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 322 (M+H+, 100).

Workup

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0200576f74047a3a46af940c7dc2e9d
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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