Tetrahydrofuran → 1-(2-Isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone

HRID 2069468Notes

Reaction equation

HRID 2069468 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([NH:13][CH:14]([CH3:16])[CH3:15])[N:7]=1)=[O:5].[CH2:18]1COCC1>C[Mg]Br.CCOCC>[CH:14]([NH:13][C:8]1[N:7]=[C:6]([C:4](=[O:5])[CH3:18])[CH:11]=[C:10]([CH3:12])[N:9]=1)([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 866453112-Isopropylamino-6-methyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide

Product 1

HCID 685106621-(2-Isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 178418573HCID 178418573, compoundSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid methoxy-methyl-amide (2.39 g, 10.0 mmol) in THF (50 mL), methyl magnesium bromide (7.0 mL of a 3 M solution in ether, 20.1 mmol) is added dropwise at 5° C. The mixture is stirred at 5° C. for 1.5 h. The reaction is quenched by adding NH4Cl. The mixture is diluted with EtOAc (75 mL), washed with sat. aq. NaHCO3, dried over Na2SO4, filtered and concentrated to give 1-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethanone (1.71 g) as a yellow solid. LC-MS: tR=0.75 min, [M+H]+=194.01; 1H NMR (CDCl3): δ 1.29 (d, J=6.5 Hz, 6H), 2.41 (s, 3H), 2.62 (s, 3H), 4.22 (m, 1H), 5.02 (m, 1H), 6.97 (s, 1H).

Workup

  1. customThe reaction is quenched
  2. additionby adding NH4Cl
  3. additionThe mixture is diluted with EtOAc (75 mL)
  4. washwashed with sat. aq. NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6bc4ff87e12b43aa97e52f9ab50c5571
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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