Triethylamine → [1-(4-Methoxyphenyl)ethyl]-2-methylpteridin-4-yl-amine

HRID 339795

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].O1CCO[CH:13](O)[CH:12]1O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([NH2:29])[CH3:28])=[CH:23][CH:22]=1.C(N(CC)CC)C>CCO.CCCCCC.CCOC(C)=O>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([NH:29][C:2]2[C:3]3[C:4](=[N:9][CH:12]=[CH:13][N:10]=3)[N:5]=[C:6]([CH3:8])[N:7]=2)[CH3:28])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 6-chloro-4,5-diamino-2-methylpyrimidine (317 mg, 2.0 mmol) and 1,4-dioxane-2,3-diol (240 mg, 2.0 mmol) in EtOH (15 mL) was stirred at 25° C. for 1 h. TLC analysis (1:1 hexane/EtOAc on SiO2) indicated complete consumption of starting material. 1-(4-Methoxyphenyl)-ethylamine (332 mg, 2.2 mmol) and triethylamine (Et3N, 0.3 mL, 2.2 mmol) were added, and the reaction was stirred overnight. The majority of solvent was removed in vacuo and the residue was partitioned between EtOAc and H2O. The organic layer was concentrated in vacuo to leave a brown residue that was purified by column chromatography over SiO2, eluting with 2:1 EtOAc/hexane, then 100% EtOAc to afford [1-(4-methoxyphenyl)ethyl]-2-methylpteridin-4-yl-amine (126 mg) as a brown oil.

Workup

customconsumption of starting material
stirringthe reaction was stirred overnight
customThe majority of solvent was removed in vacuo
customthe residue was partitioned between EtOAc and H2O
concentrationThe organic layer was concentrated in vacuo
customto leave a brown residue that
customwas purified by column chromatography over SiO2
washeluting with 2:1 EtOAc/hexane

Sources & evidence

ORD record: ord-f24ae463ec024ff493a47364f93602d2
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895568B2

Linked notes

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