Triethylamine → HCID 13338430, compound

HRID 2417661Notes

Reaction equation

HRID 2417661 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:8])[C@@H:5]([CH3:7])[NH2:6].C(N(CC)CC)C.Cl[C:17]1[C:18]2[N:26]([CH3:27])[N:25]=[C:24]([CH3:28])[C:19]=2[N:20]=[C:21]([CH3:23])[N:22]=1>CN(C)C=O>[CH3:27][N:26]1[C:18]2[C:17]([NH:6][C@H:5]([CH3:7])[C:4]([O:3][CH3:2])=[O:8])=[N:22][C:21]([CH3:23])=[N:20][C:19]=2[C:24]([CH3:28])=[N:25]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 11182647Methyl D-alaninate hydrochlorideHCID 133384077-Chloro-1,3,5-trimethyl-1H-pyrazolo[4,3-d]pyrimidine

Product 1

HCID 13338430HCID 13338430, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

D-alanine methyl ester hydrochloride (6 g, 0.043 mol) is dissolved in 30 ml of cold (5° C.) dimethylformamide and 7 ml (0.05 mol) of triethylamine is added dropwise. After stirring 15 minutes, 6 g of triethylamine hydrochloride is removed by filtering. To the filtrate is added 7 g (0.035 mol) of 7-chloro-1,3,5-trimethyl-1H-pyrazolo-[4,3-d]pyrimidine and another 6 ml of triethylamine. The mixture is stirred at 50°-55° C. for 60 hours and evaporated in vacuo. The residue is dissolved in 100 ml of methylene dichloride, washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo to give 7.6 g of slightly impure (R)-2-[1,3,5-trimethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl]aminopropionic acid, methyl ester, mp 68°-70° C. from ether as a dihydrate.

Workup

  1. additionis added dropwise
  2. custom6 g of triethylamine hydrochloride is removed
  3. filtrationby filtering
  4. stirringThe mixture is stirred at 50°-55° C. for 60 hours
  5. customevaporated in vacuo
  6. dissolutionThe residue is dissolved in 100 ml of methylene dichloride
  7. washwashed with saturated sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-000209ce74db4d59889b7b7f6f3a1b7e
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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