Hydrochloric Acid → 6,7-Bis(3-hydroxyphenyl)-pteridin-4-ylamine hydrochloride salt

HRID 1272467Notes

Reaction equation

HRID 1272467 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:15](=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)[N:14]=[CH:13][N:12]=[C:11]3[NH2:25])[CH:5]=[CH:6][CH:7]=1.[ClH:26].C(OCC)C>CO>[ClH:26].[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:15](=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)[N:14]=[CH:13][N:12]=[C:11]3[NH2:25])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 100880663-[4-Amino-7-(3-hydroxyphenyl)pteridin-6-yl]phenol

Product 1

HCID 184557376,7-Bis(3-hydroxyphenyl)-pteridin-4-ylamine hydrochloride saltYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4.4 g (13.27 mmol) of 6,7-bis(3-hydroxyphenyl)-pteridin-4-ylamine was suspended in 35 ml of MeOH. A solution of 2.61 g of aq. HCl (26.55 mmol, 12.1 N) in 5 mL of MeOH was added to the suspension. The reaction mixture became homogeneous within 5 min of stirring. It was left to stir for 30 min and then added dropwise to 400 mL of diethyl ether with vigorous stirring. The resulting precipitate was collected, washed repeatedly with ether and dried in vacuo to give 4.62 g (94.7% yield) of the product as a bright-yellow solid. 98.3% purity by LC/MS (230 DAD). Mass-spec [ES+]=332.8. 1H NMR (MeOH) 6.88–6.90 (2H, m), 6.99–7.02 (2H, m), 7.04–7.08 (2H, m), 7.17–7.20 (2H, m), 8.79 (1H, s).

Workup

  1. waitIt was left
  2. stirringto stir for 30 min
  3. customThe resulting precipitate was collected
  4. washwashed repeatedly with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3fb22f25f45f40cf86d05b25fd9bfdab
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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