Hydrochloric Acid → 2,4-Diamino-6-[2-(4-carboxyphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine

HRID 1494608Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([NH2:28])[C:5]2[CH:11]=[C:10]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([O:23]C(C)(C)C)=[O:22])=[CH:17][CH:16]=3)[CH3:14])[CH:9]=[N:8][C:6]=2[N:7]=1.Cl>[N+](C)([O-])=O>[NH2:1][C:2]1[N:3]=[C:4]([NH2:28])[C:5]2[CH:11]=[C:10]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][CH:16]=3)[CH3:14])[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension containing 4.58 g of 2,4-diamino-6-[2-(4-tert-butoxycarbonylphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine in 200 mL of a saturated solution of hydrogen chloride gas in nitromethane was stirred at 0° C. for 1 hour, and then at room temperature for 3 hours. After dilution with ether, the reaction mixture was filtered and the collected solid was washed successively with water, methanol, and acetone and then dried under reduced pressure to give 3.90 g (100%) of 2,4-diamino-6-[2-(4-carboxyphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine. NMR (DMSO-d6, 80 MHz) d 2.31(brs, 3H), 6.77 and 7.07 (brs, 1H), 7.74(d, 2H, J=8.5 Hz), 7.98(d, 2H, J=8.5 Hz), 8.26, (d, 1H, J=2.0 Hz), 8.74(d, 1H, J=2.0 Hz).

Workup

waitat room temperature for 3 hours
filtrationAfter dilution with ether, the reaction mixture was filtered
washthe collected solid was washed successively with water, methanol, and acetone
customdried under reduced pressure

Sources & evidence

ORD record: ord-9269a1071a0e4b25818d88ab25986a7f
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05026851

Reaction notes

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