Formaldehyde → HCID 178458511, compound

HRID 2082756Notes

Reaction equation

HRID 2082756 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]([C:8]2[NH:13][C:12](=[O:14])[C:11]([C:15]3[NH:19][N:18]=[N:17][N:16]=3)=[CH:10][N:9]=2)[CH:7]=1.[CH2:24]=O.O.[C:27]([BH3-])#[N:28].[Na+]>C(#N)C.C(O)(=O)C>[CH3:24][N:28]([CH3:27])[C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:21][CH2:22][CH3:23])=[C:6]([C:8]2[NH:13][C:12](=[O:14])[C:11]([C:15]3[NH:19][N:18]=[N:17][N:16]=3)=[CH:10][N:9]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 178458505HCID 178458505, compound

Product 1

HCID 178458511HCID 178458511, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-(5-amino-2-n-propoxyphenyl)-5-(5-1H-tetrazolyl)pyrimidin-4(3H)-one (0.50 g., 1.6 mmoles) in acetonitrile (40 ml.) was added 37% formaldehyde in water (1.32 ml., 16.0 mmoles). Sodium cyanoborohydride (0.302 g., 4.8 mmoles) was then added followed by glacial acetic acid (1.67 ml. The suspension was stirred at room temperature for 15 minutes and then heated under reflux for 3 hours. The mixture was cooled in an icebath. The precipitate was recrystallized from acetonitrile to give the title compound (0.19 g., 35%), m.p. 258°-259°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was cooled in an icebath
  4. customThe precipitate was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-87fb7fd4709848a6a30a710f596fa53d
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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