HCID 16750276, compound → 2-(1H-Imidazol-1-yl)-4-methyl-6-(pyrrolidin-2-yl)pyrimidine

HRID 1170473Notes

Reaction equation

HRID 1170473 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)[N:17]=1)=O)C1C=CC=CC=1>[Pd].C(O)C>[N:23]1([C:18]2[N:19]=[C:20]([CH3:22])[CH:21]=[C:16]([CH:12]3[CH2:13][CH2:14][CH2:15][NH:11]3)[N:17]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

4

Reactant 1

HCID 16750276HCID 16750276, compound

Product 1

HCID 167502772-(1H-Imidazol-1-yl)-4-methyl-6-(pyrrolidin-2-yl)pyrimidineYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (12 mg) was added to a solution of 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidine-1-carboxylic acid benzyl ester (112 mg, 0.308 mmol) and ethanol (3 mL) at rt. The reaction was vacuum purged with N2 then stirred under a balloon of H2 for 4 h. The reaction mixture was filtered through celite and concentrated. Column chromatography (10 g, DCM to 20% MeOH/DCM) afforded 63 mg (89%) of 2-imidazol-1-yl-4-methyl-6-pyrrolidin-2-yl-pyrimidine. [M+H]+ 230.16; 1H-NMR (400 MHz, CD3OD) δ 8.74 (s, 1H), 8.05 (s, 1H), 7.31 (s, 1H), 7.14 (s, 1H), 4.95 (s, 2H), 4.25 (t, 1H), 3.25 (m, 1H), 3.05 (m, 1H), 2.59 (s, 3H), 2.35 (m, 1H), 1.90 (m, 2H); 13C-NMR (100 MHz, CD3OD) δ 173.4, 170.4, 153.9, 136.0, 128.9, 116.8, 116.0, 62.1, 46.5, 32.7, 25.3, 22.7.

Workup

  1. custompurged with N2
  2. filtrationThe reaction mixture was filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3eee11838a834ceb983b16d4f6f4f694
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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