Triethylamine → HCID 117653846, compound

HRID 530096Notes

Reaction equation

HRID 530096 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C@@H:6]([CH3:13])[N:5]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:4]=2[N:3]=1.C(N(CC)CC)C.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:7](=[O:12])[C@@H:6]([CH3:13])[N:5]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 89570508HCID 89570508, compound

Product 1

HCID 117653846HCID 117653846, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (7R)-2-chloro-8-cyclohexyl-7-methyl-7,8-dihydropteridin-6(5H)-one (280 mg, 1.0 mmol) in 10 mL of dry dichloromethane was added triethylamine (1.39 mL, 10 mmol), cupric acetate (363 mg, 2.0 mmol), phenylboronic acid (244 mg, 2.0 mmol) and 4 Å molecular sieves (2.0 g). The reaction mixture was allowed to stir at room temperature with air balloon on. The reaction mixture was then filtered over Celite, washed with dichloromethane and the organic layer was washed with aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel flash chromatography, using dichloromethane-methanol mixture (v:v=99:1) as eluent, to give titled compound (yield: 39%). 1HNMR (300 MHz, CDCl3): δ 1.20-1.22 (m, 1H), 1.47-1.49 (m, 6H), 1.72-1.77 (m, 3H), 1.87-1.89 (m, 2H), 2.10-2.13 (m, 1H), 4.44-4.49 (m, 2H), 7.17 (s, 1H), 7.20-7.24 (m, 2H), 7.48-7.56 (m, 3H).

Workup

  1. filtrationThe reaction mixture was then filtered over Celite
  2. washwashed with dichloromethane
  3. washthe organic layer was washed with aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-3ede6d161c53470d89be2d453d07c414
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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