Sulfuric Acid → HCID 136358525, compound

HRID 1272469Notes

Reaction equation

HRID 1272469 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.[S:26](=[O:30])(=[O:29])([OH:28])[OH:27].C(OCC)C>CO>[S:26]([OH:30])([OH:29])(=[O:28])=[O:27].[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

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 135409495HCID 135409495, compound

Product 1

HCID 136358525HCID 136358525, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.97 g of 6,7-bis(4-hydroxyphenyl)-pteridin-4-ylamine was added to a solution of 0.585 g of concentrated sulfuric acid in 50 mL of MeOH. The homogeneous mixture was left to stir at ambient temperature for 2 hours, then it was added dropwise to 400 mL of diethyl ether. The formed orange precipitate was collected, washed repeatedly with ether and dried in vacuo to give 2.36 g (92.5% yield) of the product as a light-orange fluffy powder. 100% purity by LC/MS (230 DAD). Mass-spec [ES+]=332.8. 1H NMR (MeOH-d4) 6.77–6.80 (4H, m), 7.48–7.53 (4H, m), 8.73 (1H, s). 1H NMR (DMSO-d6) 6.76–6.81 (4H, dd), 7.41–7.47 (4H, dd), 8.84 (1H, s), 9.85 (1H, s), 10.01 (1H, s), 9.94 (1H, br.s), 10.15 (1H, br.s).

Workup

  1. waitThe homogeneous mixture was left
  2. customThe formed orange precipitate was collected
  3. washwashed repeatedly with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-cc5f1fe4c98843979932c39acd139e8d
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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