Pentylamine → Methyl 4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxybenzoate

HRID 1617154

Reaction equation

[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:7][C:8]1[N:13]=[C:12](Cl)[C:11]([CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:26][CH3:27])=[C:10]([CH3:28])[N:9]=1>CN1C(=O)CCC1.CCOC(C)=O>[NH2:7][C:8]1[N:9]=[C:10]([CH3:28])[C:11]([CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[O:26][CH3:27])=[C:12]([NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[N:13]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Pentylamine (7.2 mL) was added to a solution of the product from step (iii) (5 g) in NMP (80 mL). The resulting solution was stirred at 150° C. for 15 h. The reaction mixture was allowed to cool, diluted with EtOAc and washed with water and brine. The organic phase was dried and evaporated under reduced pressure. The residue was suspended in diethyl ether (20 mL) and the solid was collected by filtration to give the subtitle compound as a colourless solid 1.2 g that was used without further purification.

Workup

temperatureto cool
washwashed with water and brine
customThe organic phase was dried
customevaporated under reduced pressure
filtrationthe solid was collected by filtration

Sources & evidence

ORD record: ord-f1553ae66a16475982aac452b0b7a70b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765939B2

Linked notes

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