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

HRID 2387821Notes

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-4d6e5b8cbc9047adb7bd1e63e8b87862
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268990B2

Reaction notes

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