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

HRID 23196
Notes
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Reaction equation

HRID 23196 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-36964ac55df442a896fd16f1ca26f59c
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06849739B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes