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

HRID 2387812
Notes
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Reaction equation

HRID 2387812 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 689540842-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Product 1

HCID 42613073Methyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-methoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

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

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

Sources & evidence

ORD record
ord-1f3617a988a1454d81ce7d49addb3559
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268990B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes