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

HRID 2303270Notes

Reaction equation

HRID 2303270 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]

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 6228DimethylformamideSolvent

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)-6-methyl-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-9b93b76d694643dca815e7ba10d370e7
Source dataset
uspto-grants-2002_08
Patent number
US06432947B1

Reaction notes

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