Acetic Acid → N-{4-[2-(4-Amino-2-imino-2,3-dihydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl}glutamic acid

HRID 1788716Notes

Reaction equation

HRID 1788716 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:36])[C:5]2[CH:11]=[C:10]([CH2:12][CH2:13][C:14]3[CH:35]=[CH:34][C:17]([C:18]([NH:20][C@H:21]([C:29]([O:31]CC)=[O:30])[CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:19])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1.[OH-].[Na+].C(O)(=O)C>CO>[NH2:1][C:2]1[N:3]=[C:4]([NH2:36])[C:5]2[CH:11]=[C:10]([CH2:12][CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:19])=[CH:34][CH:35]=3)[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 13912568HCID 13912568, compound

Product 1

HCID 125704N-{4-[2-(4-Amino-2-imino-2,3-dihydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl}glutamic acidYield 44.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.38 g of diethyl N-(4-[2-(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate in 50 mL of methanol containing 4.6 mL of 0.5N aqueous sodium hydroxide was stirred at room temperature for 72 hours. Acetic acid (5 mL) was added, and the resulting white precipitate collected by filtration. The filter cake was washed well with water, methanol, and ether and was dried under reduced pressure to yield 0.15 g (44%) of the title compound, which can be alternatively names as 5,10-dideazaaminopterin; mp >250° C.; NMR (TFA-d1) delta 2.2-2.7 (m, 2H), 2.28; 2.7-2.95 (m, 2H), 5.0-5.2 (m, 1H), 7.35 and 7.85 (AB q, 4H, J=9 Hz), 8.7 (s, 1H), 9.1 (s, 1H).

Workup

  1. filtrationthe resulting white precipitate collected by filtration
  2. washThe filter cake was washed well with water, methanol, and ether
  3. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-86d5f7c92f124300a6300776810e38b4
Source dataset
uspto-grants-1987_08
Patent number
US04684653

Reaction notes

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