Guanidine Hydrochloride → 4-(dimethoxymethyl)pyrimidin-2-amine

HRID 552113Notes

Reaction equation

HRID 552113 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])N(C)C.[CH3:9][C:10]([CH:12](OC)OC)=O.[OH-].[Na+].Cl.[NH2:20][C:21]([NH2:23])=[NH:22]>O>[CH3:8][O:7][CH:3]([O:2][CH3:1])[C:12]1[CH:10]=[CH:9][N:22]=[C:21]([NH2:23])[N:20]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 78373Dimethylformamide dimethyl acetalHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 49130324-(dimethoxymethyl)pyrimidin-2-amineYield 36.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 5.5 mL (41 mmol, 1.0 eq.) of dimethylformamide dimethyl acetal and 5.0 mL (41 mmol, 1.0 eq.) pyruvic aldehyde dimethyl acetal was heated at 100° C. for 16 h. Methanol was removed in vacuo to afford a brown oil. A solution of 1.8 g (45 mmol, 1.1 eq.) of sodium hydroxide in 5 mL of water was added to a solution of 4.3 g (45 mmol, 1.1 eq.) of guanidine HCl in 10 mL of water. The resulting solution was added to the above described oil. The resulting mixture was stirred at room temperature for 48 h. The mixture was filtered to provide 2.5 g (15 mmol, 36%) of 2-aminopyrimidine-4-carboxaldehyde dimethylacetal (I-8).

Workup

  1. customMethanol was removed in vacuo
  2. customto afford a brown oil
  3. additionThe resulting solution was added to the
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-d31f6c9f1c634c039334b5fbae7ea635
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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