Formamide → 4-Hydroxy-7-isopropylquinazoline

HRID 605382Notes

Reaction equation

HRID 605382 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH:14]([NH2:16])=O>>[CH:11]([C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:5])[NH:16][CH:14]=[N:1]2)=[CH:7][CH:8]=1)([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 713FormamideHCID 670403622-Amino-4-isopropylbenzoic acid

Product 1

HCID 1361233184-Hydroxy-7-isopropylquinazolineYield 34%

Procedure

The product of Example 431D (0.579 g, 3.231 mmol) was reacted with formamide (1.3 mL) under a nitrogen atmosphere in a microwave (Personal Chemistry Emrys Creator, 300 W) at 150°C for 30 minutes. The cooled reaction gave a solid mass which was recrystallized from absolute ethanol (2 mL) to afford the title compound as an off-white solid (0.208 g, 1.105 mmol, 34%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.26 (d, J=6.99 Hz, 6 H) 2.91-3.21 (m, 1 H) 7.44 (dd, J=8.27, 1.65 Hz, 1 H) 7.50 (d, J=1.84 Hz, 1 H) 8.02-8.07 (m, 2 H) 12.15 (s, 1 H); MS (APCI) m/z 189 (M+H)+, 211 (M+Na)+.

Workup

  1. customThe cooled reaction
  2. customgave a solid mass which
  3. customwas recrystallized from absolute ethanol (2 mL)

Sources & evidence

ORD record
ord-34fa396468c844e4920da1d7ba884efd
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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