2-Chloroquinazolin-4-amine → HCID 9823408, compound

HRID 1274135Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4](Cl)[N:3]=1.[C:13]([O:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]>C(O)CCCC>[C:13]([O:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([C:4]3[N:3]=[C:2]([NH2:1])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=3)[CH2:28][CH2:27]2)=[CH:21][CH:20]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 120 °C

Procedure

4-amino-2-chloro-quinazoline (0.070 g, 0.39 mmol) was added to a solution of (49) (0.13 g, 0.47 mmol) in n-pentanol (5 mL) at 25° C. The mixture was heated to 120° C. and was maintained at that temperature for 12 h. The reaction mixture was then cooled to room temperature and concentrated to a brown yellow oily residue. Purification of the residue by flash column chromatography (gradient elution 0 to 5% MeOH in CH2Cl2) provided the title compound (0.12 g, 73%): TLC (Rf =0.33; 5% MeOH/CH2Cl2); 1H NMR (CDCl3) δ 7.83 (d, 2H, J=8.7), 7.51 (m, 3H), 7.10 (t, 1H, J=6.6), 6.57 (d, 2H, J=8.8), 5.35 (br s, 2H), 4.81 (d, 2H, J=13.6), 4.00 (br s, 1H), 3.60 (m, 1H), 3.14 (t, 2H, J=14.0), 2.13 (d, 2H, J=13.2), 1.57 (s, 9H), 1.47 (m, 2H); 13C NMR (CDCl3) δ 166.1, 161.6, 158.8, 152.0, 150.4, 133.2, 131.5, 125.9, 121.8, 121.3, 120.3, 111.8, 109.7, 79.9, 50.3, 42.8, 32.3, 28.3; Anal. (C24H29N5O2 ·1/4HCl)·C, H, N.

Workup

temperaturewas maintained at that temperature for 12 h
temperatureThe reaction mixture was then cooled to room temperature
concentrationconcentrated to a brown yellow oily residue
customPurification of the residue
washby flash column chromatography (gradient elution 0 to 5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-4e18f79099464338864854937477e231
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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