Triethylamine → HCID 89570511, compound

HRID 530119Notes

Reaction equation

HRID 530119 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][C:17]([F:21])([F:20])[CH2:16][CH2:15]3)[C:4]=2[N:3]=1.C(N(CC)CC)C.[C:29]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)#[N:30]>ClCCl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([C:35]3[CH:36]=[C:31]([CH:32]=[CH:33][CH:34]=3)[C:29]#[N:30])[C:7](=[O:12])[C@@H:6]([CH3:13])[N:5]([CH:14]3[CH2:15][CH2:16][C:17]([F:21])([F:20])[CH2:18][CH2:19]3)[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27343253-Cyanophenylboronic acidHCID 89570509HCID 89570509, compound

Product 1

HCID 89570511HCID 89570511, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (7R)-2-chloro-8-(4,4-difluorocyclohexyl)-7-methyl-7,8-dihydropteridin-6(5H)-one (1.80 g, 5.7 mmol) in dichloromethane (75 mL) was added triethylamine (8.07 ml, 57.8 mmol), cupric acetate (2.09 g, 11.56 mmol) and (3-cyanophenyl)boronic acid (1.69 g, 11.56 mmol) followed by 4 Å molecular sieves (2 g). The reaction mixture was stirred for 48 h at rt with an air balloon on the top. The reaction mixture was then filtered over celite to give a clear solution. The solution was washed with aqueous saturated sodium bicarbonate (50 mL×2), dried over anhydrous sodium sulfate and evaporated to give a crude material, which was then purified by silica gel column chromatography (eluent: 2% methanol in dichloromethane) to give the desired product (51%). 1HNMR (300 MHz, CDCl3): δ 1.50 (d, J=6.9 Hz, 3H), 1.80-2.24 (m, 8H), 4.40-4.61 (m, 2H), 7.20-7.26 (m, 1H), 7.47 (d, J=7.5 Hz, 1H), 7.55 (s, 1H), 7.69 (t, J=7.8 Hz, 1H), 7.80 (d, J=8.1 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was then filtered over celite
  2. customto give a clear solution
  3. washThe solution was washed with aqueous saturated sodium bicarbonate (50 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give a crude material, which
  7. customwas then purified by silica gel column chromatography (eluent: 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0c422cfee6894d61b15a9b6ac5b3733d
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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