Hydrochloric Acid → HCID 178508853, compound

HRID 1199811Notes

Reaction equation

HRID 1199811 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([OH:27])[C:5]2[CH:11]=[C:10]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([O:22]C(C)(C)C)=[O:21])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1.[N+](C)([O-])=O.Cl>CCOCC>[NH2:1][C:2]1[N:3]=[C:4]([OH:27])[C:5]2[CH:11]=[C:10]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=3)[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 178450672HCID 178450672, compound

Product 1

HCID 178508853HCID 178508853, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thirty-four milligrams of 2-amino-4-hydroxy-6-(4-tert.-butoxycarbonylphenylethynyl)pyrido[2,3-d]pyrimidine is added to 15 ml of nitromethane which has been saturated with hydrogen chloride gas at 0° C. The mixture is stirred for 1 hour. Anhydrous ether is added and the solid filtered to give 27.6 mg (62%) of 2-amino-4-hydroxy-6-(4-carboxyphenylethynyl)pyrido[2,3-d]pyrimidine as a pale yellowish solid: m.p. >260° C.; NMR (DMSO-d6, 80 MHz) delta 7.71 (d, 2H, J=8.4 Hz), 8.00 (d, 2H, J=8.4 Hz), 8.40 (d, 1H, J=2.3 Hz), 8.75 (d, 1H, J=2.3 Hz).

Workup

  1. filtrationthe solid filtered

Sources & evidence

ORD record
ord-aa0a70cd3b0c4041a6a7262dbf7579a0
Source dataset
uspto-grants-1990_02
Patent number
US04902796

Reaction notes

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