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

HRID 983711Notes

Reaction equation

HRID 983711 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-1yl)-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-d5ec8db19c8248969ad8fbfc89ca77db
Source dataset
uspto-grants-2005_03
Patent number
US06864368B2

Reaction notes

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