Lithium Hydroxide → 2-Amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acid

HRID 449339Notes

Reaction equation

HRID 449339 reaction equation
[OH-].[Li+].[NH2:3][C:4]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)[C:11]2[C:6](=[CH:7][C:8]([C:21]([O:23]C)=[O:22])=[CH:9][CH:10]=2)[N:5]=1>O.CO>[NH2:3][C:4]1[N:13]=[C:12]([N:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)[C:11]2[C:6](=[CH:7][C:8]([C:21]([OH:23])=[O:22])=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59496531Methyl 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylate

Product 1

HCID 594966492-Amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylic acidYield 110.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (29 mg, 1.2 mmol) in water (1 mL) was added to a solution of methyl 2-amino-4-(4-methylpiperazin-1-yl)quinazoline-7-carboxylate (180 mg, 0.60 mmol) in methanol (2 mL) at room temperature. The starting material was consumed after stirring for 5 h, and the reaction mixture was concentrated and dried on lyophilizer to obtain the crude product (190 mg) as an amorphous white solid. (quantitative yield). 1H NMR (300 MHz, DMSO): δ 2.22 (s, 3H), 2.48 (m, 4H), 3.49 (m, 4H), 6.23 (b, 2H), 7.55 (M, 2H), 7.75 (d, 1H); Analytic LCMS (M+H)+: m/z=288.1.

Workup

  1. customThe starting material was consumed
  2. concentrationthe reaction mixture was concentrated
  3. customdried on lyophilizer

Sources & evidence

ORD record
ord-b4da2d0af5924542bd856d5ae311c967
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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