Hydrochloric Acid → 7-[[(7R)-7-ethyl-8-isopropyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid

HRID 2364720Notes

Reaction equation

HRID 2364720 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]=2[N:3]=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:29]([OH:31])=[O:30])=[C:24]2[C:28]=1[O:27][CH2:26][CH2:25]2.Cl>C(O)C.O>[CH2:14]([C@H:6]1[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]2[N:3]=[C:2]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([C:29]([OH:31])=[O:30])=[C:24]4[C:28]=3[O:27][CH2:26][CH2:25]4)[N:11]=[CH:10][C:9]=2[N:8]([CH3:12])[C:7]1=[O:13])[CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 249683367-Amino-2,3-dihydrobenzofuran-4-carboxylic acidHCID 58405561(R)-2-Chloro-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropyrimido[4,5-b]pyrazine

Product 1

HCID 681080517-[[(7R)-7-ethyl-8-isopropyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acidYield 65.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(7R)-2-Chloro-7-ethyl-8-isopropyl-5-methyl-7H-pteridin-6-one 22d (82 mg, 3.07 mmol) and 7-amino-2,3-dihydrobenzofuran-4-carboxylic acid 22e (500 mg, 2.80 mmol) were dissolved in 34 mL of the mixture solvent of ethanol and water (V/V=1:2.4) followed by the addition of 0.4 mL of concentrated hydrochloric acid. The reaction solution was heated to reflux for 15 hours and cooled down resulting in the formation of precipitate. The precipitate was filtered to obtain the title compound 7-[[(7R)-7-ethyl-8-isopropyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid 22f (0.75 g, yield: 65.0%) as a white solid.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 15 hours
  3. temperaturecooled down
  4. customresulting in the formation of precipitate
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-5f743e0094b84f57aefe9e06c179eb17
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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