Lithium Hydroxide → HCID 135601396, compound

HRID 1072067Notes

Reaction equation

HRID 1072067 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[C:8]([CH3:17])=[C:9]2[N:14]([CH:15]=1)[N:13]=[CH:12][NH:11][C:10]2=[O:16])=[O:6]>O.C1COCC1.CO>[CH3:17][C:8]1[C:7]([C:5]([OH:6])=[O:4])=[CH:15][N:14]2[C:9]=1[C:10](=[O:16])[NH:11][CH:12]=[N:13]2

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 135510278Methyl 5-methyl-4-oxo-1,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

Product 1

HCID 135601396HCID 135601396, compoundYield 90.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A solution of LiOH (25 gm, 10 equiv) in water (416 mL) was added to a solution of 5-methyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester (23.0 gm, 0.104 mol) in a mixture of THF (1.2 L) and MeOH (0.4 L). This was heated at 65° C. for 20 h and then concentrated in vacuo to about 200 mL. Water (400 mL) was added and the pH was adjusted to 4 using conc. aqueous HCl. The precipitate was collected, washed with water, and dried to give the acid (18.2 gm, 90%). 1H NMR (MeOH-D4) δ 2.67 (s, 3H), 7.63 (s, 1H), 7.84 (s, 1H). HPLC Ret Time: 0.97 min (YMC C18 S5, 4.6×50 mm column, 3 min gradient, 4 mL/min).

Workup

  1. concentrationconcentrated in vacuo to about 200 mL
  2. additionWater (400 mL) was added
  3. customThe precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b9a0ea51d1c748e7b3fc54632a4852d0
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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