Diethyl Ether → HCID 58847283, compound

HRID 1272461Notes

Reaction equation

HRID 1272461 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15](=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[N:14]=[CH:13][N:12]=[C:11]3[NH2:25])=[CH:4][CH:3]=1.[C:26](Cl)(=[O:28])[CH3:27].[CH2:30]([O:32]CC)[CH3:31]>FC(F)(F)C(O)=O>[C:26]([O:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[N:16]=[C:15]3[C:10]([C:11]([NH2:25])=[N:12][CH:13]=[N:14]3)=[N:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([O:1][C:30](=[O:32])[CH3:31])=[CH:3][CH:4]=2)=[CH:19][CH:20]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 135409495HCID 135409495, compound

Product 1

HCID 58847283HCID 58847283, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

662.6 mg (2.0 mmol) of 6,7-bis(4-hydroxyphenyl)-pteridin-4-ylamine was dissolved in 20 ml of trifluoroacetic acid. 1.0 mL (14.06 mmol, 7.0 eq) of acetyl chloride was added via syringe to this mixture. Upon heating to 80° C. bubbling of the reaction mixture and evolution of HCl gas was observed. The reaction mixture was heated at 80° C. for 40 min, at which point LC/MS indicated a complete conversion of the starting material to the di-acetate. Solvent was removed in vacuo to give bright-yellow oil, which upon standing solidified. 40 mL of diethyl ether was added, the solid was crushed with spatula, centrifuged down, washed with 45 mL of diethyl ether twice and dried in vacuo to give 1.034 g (97.7%) of the product as a light-yellow solid. 97.5% purity by LC/MS (230 DAD). Mass-spec [ES+]=416.5. 1H NMR (DMSO-d6) 2.280 (3H, s), 2.284 (3H, s), 7.16–7.21 (4H, dd), 7.56–7.62 (4H, dd), 8.80 (1H, s), 9.46 (1H, br.s), 9.52 (1H, br, s).

Workup

  1. custombubbling of the reaction mixture and evolution of HCl gas
  2. temperatureThe reaction mixture was heated at 80° C. for 40 min, at which point LC/MS
  3. customSolvent was removed in vacuo
  4. customto give bright-yellow oil, which
  5. customthe solid was crushed with spatula
  6. washwashed with 45 mL of diethyl ether twice
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fbd3a6f05a8f4b8da24d46fffab7d97c
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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