Butylamine → Methyl 4-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzoate

HRID 2387898Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[O:20][CH3:21])=[C:4]([CH3:22])[N:3]=1.[CH2:23]([NH2:27])[CH2:24][CH2:25][CH3:26]>O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:27][CH2:23][CH2:24][CH2:25][CH3:26])[C:5]([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[O:20][CH3:21])=[C:4]([CH3:22])[N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A stirred mixture of the product from step (i) (8 g) and butylamine (7.40 ml) in dioxane (100 ml) was heated at 90° C. for 72 h. More butylamine (7.40 ml) was added and the reaction mixture stirred for a further 70 hrs. The solvent was evaporated and the crude product was purified by chromatography (5% MeOH/DCM) to afford the subtitle compound as a tan solid, 4.5 g.

Workup

customThe solvent was evaporated
customthe crude product was purified by chromatography (5% MeOH/DCM)

Sources & evidence

ORD record: ord-7a24cd76825e43ba931ff013d82ce211
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268990B2

Reaction notes

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