Diethyl Ether → 6,7-Bis(3-hydroxyphenyl)-pteridin-4-ylamine methanesulfonate salt

HRID 1272468Notes

Reaction equation

HRID 1272468 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]3[C:20](=[N:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)[N:19]=[CH:18][N:17]=[C:16]3[NH2:30])[CH:10]=[CH:11][CH:12]=1.C(OCC)C>CO>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[OH:6][C:7]1[CH:8]=[C:9]([C:13]2[N:14]=[C:15]3[C:20](=[N:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)[N:19]=[CH:18][N:17]=[C:16]3[NH2:30])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 100880663-[4-Amino-7-(3-hydroxyphenyl)pteridin-6-yl]phenol

Product 1

HCID 865941386,7-Bis(3-hydroxyphenyl)-pteridin-4-ylamine methanesulfonate saltYield 97.11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.308 g (13.63 mmol) of methanesulfonic acid in 10 mL of MeOH was added to the suspension of 2.15 g (6.48 mmol) of 6,7-bis(3-hydroxyphenyl)-pteridin-4-ylamine in 10 mL of MeOH. The mixture became homogeneous and orange-red in color. It was stirred for 30 min and then added dropwise to 400 mL of diethyl ether with vigorous stirring. The formed yellow precipitate was collected, washed with diethyl ether and dried in vacuo to give 2.69 g (97.11% yield) of the product as a light-yellow powder. Mass-spec [ES+]=332.8. 1H NMR (MeOH-d4) 2.70 (3H, s), 6.86–6.90 (2H, m), 6.99–7.01 (2H, m), 7.04–7.08 (2H, m), 7.16–7.21 (2H, m), 8.80 (1H, s).

Workup

  1. customThe formed yellow precipitate was collected
  2. washwashed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-00ca0ef48ae6460abf535c4db1d89927
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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