Hydrochloric Acid → HCID 178447251, compound

HRID 620106Notes

Reaction equation

[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:33])[C:11]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([O:28]C(C)(C)C)=[O:27])=[CH:22][CH:21]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N+](C)([O-])=O.Cl>CCOCC>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:33])[C:11]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]([OH:28])=[O:27])=[CH:24][CH:25]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

One gram of 2-pivaloylamino-4-hydroxy-6-(4-tert.butoxycarbonylphenylethynyl)pyrido[2,3-d]pyrimidine is added to 25 ml of nitromethane saturated with hydrogen chloride gas at 0° C. After stirring at 0° C., the reaction mixture is allowed to reach room temperature and stirred for an additional hour. The suspension is diluted with anhydrous ether and suction filtered. The collected solid is washed with ether, methanol, and ether again, and then dried under reduced pressure to give 0.81 g of 2-pivaloylamino-4-hydroxy-6-(4-carboxyphenylethynyl)pyrido[2,3-d]pyrimidine as a yellowish powder: m.p. >250° C.; NMR (CDCl3, 300 MHz) delta 1.25 (s, 9H), 7.72 (d, 2H, J=8.02 Hz), 7.98 (d, 2H, J=8.02 Hz), 8.52 (d, 1H, J=2.01 Hz), 9.01 (d, 1H, J=2.01 Hz); IR (KBr) 3420, 3000, 1725, 1680, 1425, 1405, 1360, 1250, 1130, 1020, and 800 cm -1.

Workup

customto reach room temperature
stirringstirred for an additional hour
filtrationfiltered
washThe collected solid is washed with ether, methanol, and ether again
customdried under reduced pressure

Sources & evidence

ORD record: ord-88f7dd9943af4d769db5aae5fa8c517f
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04818819

Reaction notes

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