Hydrochloric Acid → 2-(2-Naphthalen-2-yl-ethoxymethyl)-3H-pteridin-4-one

HRID 2076832Notes

Reaction equation

HRID 2076832 reaction equation
C([O-])([O-])=O.[K+].[K+].[NH:7]=[C:8]([NH:23][C:24]([C:26]1[C:31](Cl)=[N:30][CH:29]=[CH:28][N:27]=1)=[O:25])[CH2:9][O:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.Cl>CN(C=O)C>[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][CH2:11][O:10][CH2:9][C:8]1[NH:23][C:24](=[O:25])[C:26]2[C:31](=[N:30][CH:29]=[CH:28][N:27]=2)[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1527662053-chloro-N-[2-(2-naphthalen-2-ylethoxy)ethanimidoyl]pyrazine-2-carboxamide

Product 1

HCID 1359235352-(2-Naphthalen-2-yl-ethoxymethyl)-3H-pteridin-4-oneYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

K2CO3 (442 mg) was added to a solution of 3-chloro-pyrazine-2-carboxylic acid [1-imino-2-(2-naphthalen-2-yl-ethoxy)-ethyl]-amide (590 mg) in DMF (5 ml) and heated to 100° C. for 3 h. The reaction mixture was acidified to pH=5 (aqueous HCl, 1N) and extracted with ethyl acetate. The organic layers were dried (Na2SO4), filtered, and the solvent was evaporated. 2-(2-Naphthalen-2-yl-ethoxymethyl)-3H-pteridin-4-one (170 mg, 32%) was obtained from the residue by column chromatography (silica gel, eluent gradient n-heptane/ethyl acetate=80/20-50/50). MS: m/e=331.0 [M−H−]. 1H NMR (d6-DMSO): δ 3.09 (t, 2H), 3.91 (t, 2H), 4.51 (s, 2H), 7.45-7.50 (m, 3H), 7.79-7.88 (m, 4H), 8.82 (d, 1H), 8.99 (d, 2H), 12.72 (bs, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4d9129994a484a03b6477b73ed6ab929
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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