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

HRID 983549Notes

Reaction equation

HRID 983549 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-6a5ae218d1574defa1680e3c7bff8d45
Source dataset
uspto-grants-2005_03
Patent number
US06864263B2

Reaction notes

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