Hydrochloric Acid → 4-[[(2,4-Diamino-5-methylpyrido[2,3-d]pyrimidin-6-yl)methyl]ethylamino]benzoyl-L-glutamic acid

HRID 4450Notes

Reaction equation

C([O:3][C:4](=[O:39])[C@H:5]([CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])[NH:6][C:7](=[O:31])[C:8]1[CH:13]=[CH:12][C:11]([N:14]([CH2:17][C:18]2[CH:29]=[N:28][C:21]3[N:22]=[C:23]([NH2:27])[N:24]=[C:25]([NH2:26])[C:20]=3[C:19]=2[CH3:30])[CH2:15][CH3:16])=[CH:10][CH:9]=1)C.COC(=O)[C@H](CCC(OC)=O)NC(=O)C1C=CC(N(CC2C=NC3N=C(N)N=C(N)C=3C=2C)C)=CC=1.Cl.[OH-].[Na+]>>[NH2:27][C:23]1[N:24]=[C:25]([NH2:26])[C:20]2[C:19]([CH3:30])=[C:18]([CH2:17][N:14]([CH2:15][CH3:16])[C:11]3[CH:12]=[CH:13][C:8]([C:7]([NH:6][C@H:5]([C:4]([OH:39])=[O:3])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[O:31])=[CH:9][CH:10]=3)[CH:29]=[N:28][C:21]=2[N:22]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 54044906N-[4-[[(2,4-Diamino-5-methylpyrido[2,3-d]pyrimidin-6-yl)methyl]methylamino]benzoyl]-L-glutamic Acid Dimethyl Ester

HCID 131715453HCID 131715453, compound

Product 1

HCID 138447394-[[(2,4-Diamino-5-methylpyrido[2,3-d]pyrimidin-6-yl)methyl]ethylamino]benzoyl-L-glutamic acidYield 97%

Procedure

N-[4-[[(2,4-Diamino-5-methylpyrido[2,3-d]pyrimidin-6-yl)methyl]ethylamino]benzoyl-L-glutamic acid (21, 5-Methyl-5-deaza-10-ethylaminopterin) was prepared by saponification of 19 as described for the conversion of 18 to 20; yield 97% (56 mg from 60 mg, 0.109 mmol), of 19·0.6H2O, homogeneous by HPLC. Spectral data: mass, m/e 482 (M+1)+ ; UV, 0.1N HCl, 228 (40.8), 313 (17.1; pH 7, 227 (39.2), 308 (30.2); 0.1N NaOH, 228 (36.0), 308 (29.0).

Sources & evidence

ORD record: ord-ec77ee8ce6d54d51817a1b5b60ea9228
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04725687

Reaction notes

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