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

HRID 983710Notes

Reaction equation

HRID 983710 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-33761ff50ea74a528e24c3f7e41e45c3
Source dataset
uspto-grants-2005_03
Patent number
US06864368B2

Reaction notes

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