Pyridine → 2-Isopropylamino-6-methyl-pyrimidine-4-carbonitrile

HRID 2069422Notes

Reaction equation

HRID 2069422 reaction equation
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([NH2:13])=O)[CH:8]=[C:7]([CH3:14])[N:6]=1)([CH3:3])[CH3:2].N1C=CC=CC=1>C(Cl)Cl>[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]#[N:13])[CH:8]=[C:7]([CH3:14])[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1049PyridineHCID 685093012-Isopropylamino-6-methyl-pyrimidine-4-carboxylic acid amide

Product 1

HCID 685082172-Isopropylamino-6-methyl-pyrimidine-4-carbonitrileYield 249.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid amide (1.24 g, 6.4 mmol) in DCM (20 mL), pyridine (2.53 mL, 25.6 mmol) is added followed by TFFA (2.7 mL, 19.2 mmol). The reaction mixture is stirred for 4 h, and then is quenched with water. The mixture is extracted with DCM. The org. phase is washed with sat. aq. NaHCO3 and dried over MgSO4, filtered and evaporated. Purification by CC on silica gel (eluting with Heptane/EtOAc 4:1) affords the 2-isopropylamino-6-methyl-pyrimidine-4-carbonitrile as a yellow oil (2.81 g); LC-MS: tR=0.89; [M+H]+=177.04.

Workup

  1. additionis added
  2. customis quenched with water
  3. extractionThe mixture is extracted with DCM
  4. washphase is washed with sat. aq. NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by CC on silica gel (eluting with Heptane/EtOAc 4:1)

Sources & evidence

ORD record
ord-13eae6f1fb91407c9a1179df01e6dc6b
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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