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

HRID 1617167Notes

Reaction equation

S(=O)(=O)(O)O.[NH2:6][C:7]1[N:12]=[C:11]([CH3:13])[C:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:17][C:16]=2[F:25])=[C:9]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[N:8]=1.[C:32]([O-])(O)=O.[Na+]>CO.O>[NH2:6][C:7]1[N:12]=[C:11]([CH3:13])[C:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:32])=[O:23])=[CH:17][C:16]=2[F:25])=[C:9]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[N:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Sulfuric acid (3 ml) was added to a solution of the product from step (viii) (0.54 g) in MeOH (6 mL). The mixture was heated to 70° C. for 2 h and allowed to cool. The mixture was diluted with cold water (10 mL) and the pH adjusted to ˜7 using NaHCO3. The aqueous phase was extracted with EtOAc and the combined organic phase was dried, filtered and evaporated. The crude product was purified by RPHPLC to afford the title compound as a colourless solid 0.08 g.

Workup

temperatureto cool
extractionThe aqueous phase was extracted with EtOAc
customthe combined organic phase was dried
filtrationfiltered
customevaporated
customThe crude product was purified by RPHPLC

Sources & evidence

ORD record: ord-2c236976fd3746f2aa6e9ba60dd63015
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765939B2

Reaction notes

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