HCID 59465198, compound → HCID 25158232, compound

HRID 1714837Notes

Reaction equation

HRID 1714837 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH2:15][C:16]2[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=2)[C@@H:9]([CH3:14])[C:10]([O:12]C)=O)[C:5]([N+:26]([O-])=O)=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[NH:26][C:10](=[O:12])[C@H:9]([CH3:14])[N:8]([CH2:15][C:16]3[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=3)[C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 59465198HCID 59465198, compound2×

Product 1

HCID 25158232HCID 25158232, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Methyl (2S)-2-[(2-amino-5-nitro-pyrimidin-4-yl)-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methyl]amino]propanoate (Intermediate 1)(500 mg, 1.28 mmol) was dissolved in acetic acid (4 mL) and heated to 70° C., then iron powder (144 mg, 2.58 mmol) was added. The mixture was stirred at 70° C. for 1 hour, then 100° C. for 30 minutes. The dark mixture was filtered through Celite®, and the filter media was washed with DCM. The filtrate was concentrated under reduced pressure, then purified by column chromatography (eluting with 5-20% methanol in DCM) to yield the title product as a cream foam (354 mg, 84%);

Workup

  1. wait100° C. for 30 minutes
  2. filtrationThe dark mixture was filtered through Celite®
  3. washthe filter media was washed with DCM
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by column chromatography (eluting with 5-20% methanol in DCM)

Sources & evidence

ORD record
ord-ad27efa55a3c48169d604957067dd695
Source dataset
uspto-grants-2010_09
Patent number
US07799781B2

Reaction notes

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