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

HRID 231302Notes

Reaction equation

HRID 231302 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 named 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-d510836079bc44d0b4d8bc83bc837edc
Source dataset
uspto-grants-1989_07
Patent number
US04845216

Reaction notes

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