Triethylamine → HCID 117653837, compound

HRID 530102Notes

Reaction equation

HRID 530102 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]([CH3:14])([CH3:13])[N:5]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[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:6]([CH3:13])([CH3:14])[N:5]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 85994846HCID 85994846, compound

Product 1

HCID 117653837HCID 117653837, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-chloro-7,7-dimethyl-8-(3-methylbutyl)-7,8-dihydropteridin-6(5H)-one (707 mg, 2.5 mmol) in dichloromethane (50 mL) was added triethylamine (25.0 mmol), cupric acetate (908 mg, 5.0 mmol) and phenylboronic acid (610 mg, 5.0 mmol) followed by 4 Å molecular sieves (2.0 g). The reaction mixture was stirred for 48 h at room temperature with an air balloon. Then the reaction mixture was filtered over celite. The filtrate was washed with aqueous saturated sodium bicarbonate (2×30 mL), dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography on silica gel (Eluent: 2% methanol in dichloromethane) to give titled product (yield; 46%). 1HNMR (300 MHz, CDCl3): δ 1.0 (s, 3H), 1.02 (s, 3H), 1.61-1.65 (m, 9H), 3.64 (q, J=5.1 Hz, 2H), 7.06 (s, 1H), 7.18-7.21 (m, 2H) and 7.48-7.57 (m, 3H).

Workup

  1. filtrationThen the reaction mixture was filtered over celite
  2. washThe filtrate was washed with aqueous saturated sodium bicarbonate (2×30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (Eluent: 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0491f6d226c04da98212240f84c75d13
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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