Hydrochloric Acid → 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl4-pyrimidinyl]amino]acetic acid

HRID 2303269Notes

Reaction equation

HRID 2303269 reaction equation
[C:1]([CH2:3][CH2:4][N:5]([C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[N:13]=1)[CH2:6][C:7]([O:9]CC)=[O:8])#[N:2].[Li+].[OH-].O.Cl>C1COCC1>[C:1]([CH2:3][CH2:4][N:5]([C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[N:13]=1)[CH2:6][C:7]([OH:9])=[O:8])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 865863382-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl ester

Product 1

HCID 224876012-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl4-pyrimidinyl]amino]acetic acidYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl ester (4.51 g, 14.4 mmol) dissolved in THF (250 mL) was added LiOH (0.91 g, 21.7 mmol) and water (30 mL). After stirring for 18 hours, most of the solvent was removed in vacuo and 1 N HCl (21.7 mL, 21.7 mmol) was added. The solid that formed was suction filtered and collected on paper to give 3.17 g of 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid (a compound of formula (Yc2)).

Workup

  1. additionwas added
  2. customThe solid that formed
  3. filtrationfiltered
  4. customcollected on paper

Sources & evidence

ORD record
ord-4c30f58434e54a378122ab8172cecd62
Source dataset
uspto-grants-2002_08
Patent number
US06432947B1

Reaction notes

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