Acetic Acid → HCID 59184845, compound

HRID 426287Notes

Reaction equation

HRID 426287 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:10]([C:14]2[N:15]([CH2:25][C:26]3[CH:31]=[C:30]([NH:32]CC4C=CC(OC)=CC=4)[N:29]=[C:28]([F:42])[CH:27]=3)[C:16](=[O:24])[NH:17][C:18](=[O:23])[C:19]=2[CH:20]([CH3:22])[CH3:21])[C:11](=[O:13])[CH3:12])[CH:6]=[C:7]([CH3:9])[CH:8]=1)#[N:2].C(O)(=O)C.[N+]([O-])([O-])=O.[NH4+]>C(#N)C.O>[NH2:32][C:30]1[CH:31]=[C:26]([CH2:25][N:15]2[C:14]([N:10]([C:5]3[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)[C:11](=[O:13])[CH3:12])=[C:19]([CH:20]([CH3:22])[CH3:21])[C:18](=[O:23])[NH:17][C:16]2=[O:24])[CH:27]=[C:28]([F:42])[N:29]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 22985Ammonium nitrateHCID 59184842HCID 59184842, compound

Product 1

HCID 59184845HCID 59184845, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of N-(3-cyano-5-methyl-phenyl)-N-{3-[2-fluoro-6-(4-methoxy-benzylamino)-pyridin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl}-acetamide (58 mg, 0.10 mmol) in acetonitrile (0.7 mL) was treated with glacial acetic acid (0.275 mL), cerric (IV) ammonium nitrate (111 mg, 0.20 mmol) and water (10 drops). After 30 min the mixture was partitioned between water (5 mL) and ethyl acetate (10 mL). The solvent was removed from the organic phase in vacuo and the residue was subjected to flash chromatography (eluant: 0-70% ethyl acetate/hexanes). The product containing fractions were combined and the solvent was removed in vacuo to yield the product (23 mg, 0.051 mmol). C23H23FN6O3 calculated 450.2, observed [M+1]+451.1; rt=3.08 min.

Workup

  1. customAfter 30 min the mixture was partitioned between water (5 mL) and ethyl acetate (10 mL)
  2. customThe solvent was removed from the organic phase in vacuo
  3. additionThe product containing fractions
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8d0a0c7bc2c84fafac5cdb31c4f2b697
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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