Sulfuric Acid → (S)-Methyl 2-(4-((2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetate

HRID 1617184Notes

Reaction equation

HRID 1617184 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[N:12]=[C:11]([NH:13][C@@H:14]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][CH2:16][OH:17])[C:10]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][C:24]=2[F:33])=[C:9]([CH3:34])[N:8]=1.[C:35]([O-])(O)=O.[Na+]>CO.O>[NH2:6][C:7]1[N:12]=[C:11]([NH:13][C@@H:14]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][CH2:16][OH:17])[C:10]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32][CH3:35])=[O:31])=[CH:25][C:24]=2[F:33])=[C:9]([CH3:34])[N:8]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 68956559(S)-2-(4-((2-Amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetic acid

Product 1

HCID 42613160(S)-Methyl 2-(4-((2-amino-4-(1-hydroxyheptan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-fluorophenyl)acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Concentrated sulfuric acid (0.3 mL) was added to a stirred solution of the product from step (v) (0.08 g) in MeOH (1 mL) and the mixture was heated to 70° C. for 2 h. The mixture was allowed to cool, diluted with water (2 mL) and neutralised with NaHCO3. The aqueous was extracted with EtOAc and the combined organic phase was dried and evaporated. The crude product was purified by RPHPLC to give the title compound, 0.005 g.

Workup

  1. temperatureto cool
  2. extractionThe aqueous was extracted with EtOAc
  3. customthe combined organic phase was dried
  4. customevaporated
  5. customThe crude product was purified by RPHPLC

Sources & evidence

ORD record
ord-5db57e1a9685467eb833aa6ea18e9022
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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