1-Butanol → HCID 22048115, compound

HRID 1759749Notes

Reaction equation

[NH:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10](Cl)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=1.Cl.[CH2:26]([OH:30])[CH2:27]CC>CO>[NH:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10]([NH:16][C:17]2[CH:24]=[CH:23][C:20]([CH2:21][O:22][CH2:27][CH2:26][OH:30])=[CH:19][CH:18]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Anilino-5-bromo-2-chloropyrimidine (Method 1, 2.0 g, 7.03 mmol) was dissolved in n-butanol (40 ml) and methanol (10 ml). 4-Aminobenzyl alcohol (778 mg, 6.33 mmol) and ethereal hydrogen chloride (1.0M; 6.33 ml, 6.33 mmol) were added and the solution was heated at 100° C. for 20 hours. Volatile material was removed by evaporation and the residue as dissolved in ethylene glycol (20 ml). The solution was heated at 100° C. for 6 hours and volatile material was removed by evaporation. The residue was purified by column chromatography, eluting with 0-4% methanol solution in DCM containing 0.5% aqueous ammonia solution, to give the product as a white solid (550 mg, 19%). NMR: 3.40 (t, 2H), 3.50 (dt, 2H), 4.37 (s, 2H), 4.57 (t, 1H), 7.09 (d, 2H), 7.10 (s, 1H), 7.15 (t, 1H), 7.36 (dd, 2H), 7.54 (d, 2H), 7.60 (d, 2H), 8.09 (s, 1H), 8.54 (s, 1H), 9.29 (s, 1H); MS (MH+): 415.2, 417.2.

Workup

customVolatile material was removed by evaporation
dissolutionthe residue as dissolved in ethylene glycol (20 ml)
temperatureThe solution was heated at 100° C. for 6 hours
customvolatile material was removed by evaporation
customThe residue was purified by column chromatography
washeluting with 0-4% methanol solution in DCM containing 0.5% aqueous ammonia solution

Sources & evidence

ORD record: ord-4cae1c54a6584d1e85114546fece0d6b
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838464B2

Reaction notes

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