Water → HCID 11531856, compound

HRID 1170477Notes

Reaction equation

HRID 1170477 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH:13]3[CH2:17][CH2:16][CH2:15][NH:14]3)[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:18]1[O:31][C:30]2[CH:29]=[CH:28][C:22]([CH2:23][CH2:24][N:25]=[C:26]=[O:27])=[CH:21][C:20]=2[O:19]1.C(N(CC)CC)C.O>C1COCC1>[O:31]1[C:30]2[CH:29]=[CH:28][C:22]([CH2:23][CH2:24][NH:25][C:26]([N:14]3[CH2:15][CH2:16][CH2:17][CH:13]3[C:8]3[CH:9]=[C:10]([CH3:12])[N:11]=[C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[N:7]=3)=[O:27])=[CH:21][C:20]=2[O:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 44186063,4-Methylenedioxyphenethyl isocyanateHCID 167502772-(1H-Imidazol-1-yl)-4-methyl-6-(pyrrolidin-2-yl)pyrimidine

Product 1

HCID 11531856HCID 11531856, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-imidazol-1-yl-4-methyl-6-pyrrolidin-2-yl-pyrimidine (21.8 mg, 0.095 mmol), 3,4-methylenedioxyphenethyl isocyanate (29 mg, 0.151 mmol) and triethylamine (0.4 mL) in anhydrous THF (1.5 mL) was reacted for 10 min. Water was added and the solution was extracted with ethyl acetate (2×3 mL), washed with brine and dried over Na2SO4. Evaporation of the solvent and purification by TLC plate gave 36 mg (90%) of 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidine-1-carboxylic acid (2-benzo[1,3]dioxol-5-yl-ethyl)-amide as a white solid. [M+H]+ 421.15; 1H-NMR (400 MHz, CD3OD) δ 8.65 (s, 1H), 7.99 (s, 1H), 7.14 (s, 1H), 7.11 (s, 1H), 6.65 (m, 3H), 5.88 (s, 2H), 4.98 (m, 1H), 3.62 (m, 1H), 3.55 (m, 1H), 3.34 (m, 2H), 2.69 (m, 2H), 2.56 (s, 3H), 2.41 (m, 1H), 2.03 (m, 3H); 13C-NMR (100 MHz, CD3OD) δ 173.9, 170.3, 166.5, 157.7, 147.6, 145.9, 133.2, 128.9, 121.3, 115.0, 108.6, 107.6, 106.9, 61.4, 46.4, 41.8, 35.7, 32.4, 23.3, 22.8.

Workup

  1. extractionthe solution was extracted with ethyl acetate (2×3 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent and purification by TLC plate

Sources & evidence

ORD record
ord-c0ae83d388e944788c5915fbaf138fbf
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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