Formic Acid → HCID 178420877, compound

HRID 1848115Notes

Reaction equation

HRID 1848115 reaction equation
[N:1]1[CH:6]=[C:5]([NH2:7])[C:4]([NH2:8])=[N:3][CH:2]=1.[CH:9](O)=O>C(OC(OCC)OCC)C>[N:1]1[CH:6]=[C:5]2[C:4]([NH:8][CH:9]=[N:7]2)=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 837034,5-Diaminopyrimidine

Product 1

HCID 178420877HCID 178420877, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

A solution of pyrimidine-4,5-diamine (718 mg, 6.53 mmol) and HCOOH (0.36 mL) in triethoxymethane (19 mL) was stirred at 90° C. for 3.5 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 40:1 DCM/MeOH to give 9H-purine as a brown solid (784 mg, 100%). 1H NMR (300 MHz, DMSO-d6) δ 13.40 (br s, 1H), 9.12 (s, 1H), 8.92 (s, 1H), 8.60 (s, 1H). LCMS (ESI) m/z 121 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with 40:1 DCM/MeOH

Sources & evidence

ORD record
ord-5a811a9e090b461aa5d6f0d83c1c12ff
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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