Formic Acid → 7-Amino-2-benzylaminopyrido[4,3-d]pyrimidine

HRID 1281950Notes

Reaction equation

[C:1]([O-])(=O)C.[NH2:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([C:13]#[N:14])=[CH:8][NH+:7]=1.C(O)=O.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[NH2:5][C:6]1[N:7]=[CH:8][C:9]2[CH:13]=[N:14][C:1]([NH:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:12][C:10]=2[CH:11]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2,4-diamino,5-cyanopyridinium acetate (8.78 g, 45 mmol), formic acid (10.66 g, 0.204 mol) and benzylamine (45 mL, 0.41 mol) is heated at 200° C. under N2 for 2 h. Upon cooling, it solidifies. Water (500 mL) is added and the gummy solid/water mixture is stirred for −20 min. at 0° C. The liquid is decanted. The solid is washed with water and then recrystallized from isopropanol (25 mL). After drying in a vacuum oven overnight, 7-amino-2-benzylaminopyrido[4,3-d]pyrimidine (8.29 g, 73%) is obtained as a light yellow solid. 1H NMR (DMSO) δ 9.10 (1H, s), 8.85 (1H, t, J=5.8 Hz), 8.25 (1H, s), 7.21-7.36 (5H, m), 6.46 (2H, brs), 6.35 (1H, s), 4.74 (2H, d, J=6.0 Hz).

Workup

temperatureUpon cooling
customThe liquid is decanted
washThe solid is washed with water
customrecrystallized from isopropanol (25 mL)
customAfter drying in a vacuum oven overnight

Sources & evidence

ORD record: ord-2906ff0bd38044f28dc09f3f53cd4a2a
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455534B2

Reaction notes

Loading…