Isopropylethylamine → HCID 178463613, compound

HRID 1056376Notes

Reaction equation

HRID 1056376 reaction equation
[CH2:1]([NH:3][CH:4]([CH3:6])[CH3:5])[CH3:2].[Br:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15](Cl)[N:14]=[C:13]2[OH:19]>>[Br:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([N:3]([CH2:1][CH3:2])[CH:4]([CH3:6])[CH3:5])[N:14]=[C:13]2[OH:19]

Participants

3

Reactant 2

HCID 88318IsopropylethylamineHCID 178517813HCID 178517813, compound

Product 1

HCID 178463613HCID 178463613, compoundYield 97.1%

Conditions

Temperature
170 °C

Procedure

A slurry of N-ethylisopropylamine (1.40 mL, 11.56 mmol) and 8-bromo-2-chloroquinazolin-4-ol (407c; 0.10 g, 0.385 mmol) was sealed in a microwave tube and heated to 170° C. for 30 min. The reaction was judged complete and clean. The reaction was partitioned between satd aq ammonium chloride and DCM. The aqueous layer was extracted with DCM 3 times, and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-2-(ethyl(isopropyl)amino)quinazolin-4-ol (0.116 g, 0.374 mmol, 97% yield) as a brown semi-solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.87 (2H, m), 6.96 (1H, t, J=7.7 Hz), 4.81 (1H, dt, J=13.4, 6.7 Hz), 3.51 (2H, q, J=7.0 Hz), 1.13-1.24 (9H, m). m/z (ESI, +ve ion) 310.0/312.0 (M+H)+.

Workup

  1. customThe reaction was partitioned between satd aq ammonium chloride and DCM
  2. extractionThe aqueous layer was extracted with DCM 3 times
  3. dry with materialthe combined organics were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ef39780f3e54ff4ad2d6cb53d2f144b
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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