Formic Acid → 1,3-Dicyclopropylmethyl xanthine

HRID 1860978

Reaction equation

[CH:1]1([CH2:4][N:5]2[C:12]([NH2:13])=[CH:11][C:9](=[O:10])[N:8]([CH2:14][CH:15]3[CH2:17][CH2:16]3)[C:6]2=[O:7])[CH2:3][CH2:2]1.N([O-])=O.[Na+].C(O)=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH:33]([NH2:35])=O>>[CH:15]1([CH2:14][N:8]2[C:9](=[O:10])[C:11]3[NH:35][CH:33]=[N:13][C:12]=3[N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:6]2=[O:7])[CH2:17][CH2:16]1

Participants

Reactant 5

HCID 284Formic Acid

HCID 713Formamide

HCID 24489Sodium Dithionite

HCID 186245156-Amino-1,3-bis(cyclopropylmethyl)uracil

HCID 23668193Sodium Nitrite

Product 1

HCID 152913031,3-Dicyclopropylmethyl xanthine

Conditions

Temperature: 100 °C

Procedure

1,3-Di-cyclopropylmethyl xanthine was prepared using an analogous procedure to that described in Chem. Berichte 88, 1306-1312, 1955: 20.2 g (0.0855 mol) of 1,3-di-cyclopropylmethyl-6-amino-uracil was dissolved in 100 ml of formamide, then 5.9 g sodium nitrite was added and at 60° C. 13.4 ml formic acid was added slowly with stirring. After the colour had changed from yellow to violet, the mixture was heated up to 100° C. and 3.1 g of sodium dithionite (Na2S2O4) was added in small portions.

Sources & evidence

ORD record: ord-59b89dff20d94e4787708adca486d9c2
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531600B1

Linked notes

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