Triethylamine → HCID 13338425, compound

HRID 2417664Notes

Reaction equation

HRID 2417664 reaction equation
Cl[C:2]1[C:3]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[NH2:14][C@H:15]([CH2:19][OH:20])[CH:16]([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C)C=O>[CH3:12][N:11]1[C:3]2[C:2]([NH:14][CH:15]([CH:16]([CH3:18])[CH3:17])[CH2:19][OH:20])=[N:7][C:6]([CH3:8])=[N:5][C:4]=2[C:9]([CH3:13])=[N:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 640993L-ValinolHCID 133384077-Chloro-1,3,5-trimethyl-1H-pyrazolo[4,3-d]pyrimidine

Product 1

HCID 13338425HCID 13338425, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8 g (0.04 mol) of 7-chloro-1,3,5-trimethyl-1H-pyrazolo[4,3-d]pyrimidine (Ex. 3), 4.5 g (0.045 mol) of L-valinol (2-amino-3-methyl-1-butanol) and 8 ml of triethylamine in 50 ml of dimethylformamide is stirred at 50°-55° C. for 50 hours and evaporated in vacuo. The residue is dissolved in methylene dichloride, washed with a saturated solution of sodium bicarbonate, dried over MgSO4, and evaporated in vacuo. The residue is stirred in pet ether to give 4.8 g (45%) of 2-[1,3,5-trimethyl-1H-pyrazolo[4,3-d]-pyrimidine-7-yl]amino-3-methyl-1-butanol, mp 166°-168° C. from acetonitrile.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue is dissolved in methylene dichloride
  3. washwashed with a saturated solution of sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. stirringThe residue is stirred in pet ether

Sources & evidence

ORD record
ord-268dad0f07be42a0bc82a707200e1df9
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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