Sulfuric Acid → Methyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetate

HRID 1617158Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#N)=[CH:12][C:11]=2[O:19][CH3:20])=[C:4]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:3]=1.S(=O)(=O)(O)[OH:28].[C:32]([O-])(O)=[O:33].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:33][CH3:32])=[O:28])=[CH:12][C:11]=2[O:19][CH3:20])=[C:4]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The product from step (vii) (0.329 g) was added in one portion to a mixture of sulfuric acid (2 ml) and MeOH (4 mL). The resulting solution was stirred at 70° C. for 2 h. The mixture was allowed to cool and poured into saturated aqueous NaHCO3 (20 mL). The aqueous was extracted with EtOAc and the combined organic phase was dried, filtered and evaporated. The crude product was purified by RPHPLC to afford a colourless gum that was triturated with hexane (5 mL). The solid was collected by filtration to give the title compound as a colorless solid 0.089 g.

Workup

temperatureto cool
extractionThe aqueous was extracted with EtOAc
customthe combined organic phase was dried
filtrationfiltered
customevaporated
customThe crude product was purified by RPHPLC
customto afford a colourless gum that
customwas triturated with hexane (5 mL)
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-9d4b25aef539408799e4c9b7bb61595c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765939B2

Reaction notes

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