Formaldehyde → HCID 18767636, compound

HRID 395887Notes

Reaction equation

HRID 395887 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]=[CH:9][NH:8][C:7]=2[N:6]([CH2:14][CH2:15][CH3:16])[C:5]1=[O:17])[CH2:2][CH3:3].[CH2:18]=O.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>CCO>[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:18][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:9]=[N:8][C:7]=2[N:6]([CH2:14][CH2:15][CH3:16])[C:5]1=[O:17])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 178456514HCID 178456514, compound

Product 1

HCID 18767636HCID 18767636, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,3-dipropyl-3,9-dihydro-purine-2,6-dione (446 mg, 1.89 mmol), 37% aqueous formaldehyde (1.2 eq, 2.26 mmol, 0.190 ml) and pyrrolidine (1.2 eq, 2.26 mmol, 161 mg) in EtOH (25 ml) was heated at relux for 36 h. The cool reaction mixture was concentrated in vacuo to give a solid that was dried in vacuo for 24 h (598 mg, 99%). 1H NMR (300 MHz, CDCl3); d 0.94 (coincident t, 6H), 1.64 (m, 2H), 1.75 (m, 4H), 1.78 (m, 2H, partially-obscured), 2.69 (m, 2H), 4.00 (m, 4H), 5.30 (s, 2H), 7.59 (s, 1H); MS: 320 (MH+).

Workup

  1. customThe cool reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customto give a solid
  4. customthat was dried in vacuo for 24 h (598 mg, 99%)

Sources & evidence

ORD record
ord-e8f88353c2364ab5bfe8882251a9f9f0
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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