Triethylamine → 2-chloro-7-methyl-5,8-diphenyl-7,8-dihydropteridin-6(5H)-one

HRID 530111Notes

Reaction equation

HRID 530111 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]([CH3:13])[N:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH: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])[CH:6]([CH3:13])[N:5]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 895608352-chloro-7-methyl-8-phenyl-7,8-dihydropteridin-6(5H)-one

Product 1

HCID 895703912-chloro-7-methyl-5,8-diphenyl-7,8-dihydropteridin-6(5H)-oneYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-chloro-7-methyl-8-phenyl-7,8-dihydropteridin-6(5H)-one (1.59 g, 5.78 mmol) in dichloromethane (75 mL) was added triethylamine (8.07 ml, 57.8 mmol), cupric acetate (2.09 g, 11.56 mmol) and phenylboronic acid (1.41 g, 11.56 mmol) followed by 4 Å molecular sieves (2 g). The resulting 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 (750 mg, 37%). 1HNMR (300 MHz, CDCl3): δ 1.65 (d, J=6.9 Hz, 3H), 4.82 (q, J=6.9 Hz, 1H) and 7.36-7.65 (m, 11H).

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-080b5a100755434693f4e915db85f75c
Source dataset
uspto-grants-2016_05
Patent number
US09351974B2

Reaction notes

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