Carbon Dioxide → 3-[4-Amino-7-(3-hydroxyphenyl)pteridin-6-yl]phenol

HRID 1272466Notes

Reaction equation

S(O)(O)(=O)=O.[NH2:6][C:7]1[C:12]([NH2:13])=[C:11]([NH2:14])[N:10]=[CH:9][N:8]=1.C(=O)(O)[O-].[Na+].C(=O)=O.[OH:23][C:24]1[CH:25]=[C:26]([C:30]([C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([OH:40])[CH:35]=2)=O)=O)[CH:27]=[CH:28][CH:29]=1>O>[OH:23][C:24]1[CH:25]=[C:26]([C:30]2[N:13]=[C:12]3[C:11](=[N:14][C:32]=2[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([OH:40])[CH:35]=2)[N:10]=[CH:9][N:8]=[C:7]3[NH2:6])[CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2.23 g (10.0 mmol) of 4,5,6-triaminopyrimidine sulfate was added in small portions to a solution of 1.68 g (20.0 mmol) sodium bicarbonate in 50 mL of water with vigorous stirring. A brisk evolution of CO2 gas was observed. The resulting suspension was heated to 80° C. and 2.42 g (10 mmol) of 3,3′-dihydroxybenzil was added to the mixture. The reaction mixture was refluxed for 1 hour, during which time the starting materials completely dissolved and the product precipitated out as a light-yellow solid.

Workup

temperatureThe reaction mixture was refluxed for 1 hour, during which time the starting materials
dissolutioncompletely dissolved
customthe product precipitated out as a light-yellow solid

Sources & evidence

ORD record: ord-1a34e0730189408fb889f05eedd0d6ad
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208493B2

Reaction notes

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