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Diethylamine → 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino)-N,N-diethylacetamide

HRID 352628
Notes
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Reaction equation

HRID 352628 reaction equation
[C:1]([CH2:3][CH2:4][N:5]([C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[N:11]=1)[CH2:6][C:7]([OH:9])=O)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:34]([NH:36][CH2:37][CH3:38])[CH3:35]>CN(C=O)C>[C:1]([CH2:3][CH2:4][N:5]([C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[N:11]=1)[CH2:6][C:7]([N:36]([CH2:37][CH3:38])[CH2:34][CH3:35])=[O:9])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 224876012-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl4-pyrimidinyl]amino]acetic acid

Product 1

HCID 224881192-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino)-N,N-diethylacetamideYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid (1.53 g, 5.3 mmol) slurried in DMF (25 mL) was added carbonyldiimidazole (0.87 g, 5.4 mmol). After stirring for 2 hours, diethylamine (1.0 mL, 9.7 mmol) (a compound of formula Y4)) was added. After stirring for 18 hours, the reaction was partitioned with ethyl acetate and water. The organic layer was separated, dried (Na2SO4), and the solvent was removed in vacuo to give 0.91 g of 2-[(2-cyanoethyl)[2-(1H-imidazol-1-yl)-6methyl-4-pyrimidinyl]amino)-N,N-diethylacetamide (a compound of formula (Yc3)).

Workup

  1. stirringAfter stirring for 18 hours
  2. customthe reaction was partitioned with ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d6d5a37fe7e04363a8446446afbd4ce0
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747031B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes