Acetic Acid → N-Cyclopentyl-N'-(2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl)-ethane-1,2-diamine

HRID 1016462Notes

Reaction equation

HRID 1016462 reaction equation
[CH3:1][C:2]1[CH:15]=[C:5]2[N:6]=[C:7]([CH3:14])[CH:8]=[C:9]([NH:10][CH2:11][CH2:12][NH2:13])[N:4]2[N:3]=1.[C:16]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:16]1([NH:13][CH2:12][CH2:11][NH:10][C:9]2[N:4]3[N:3]=[C:2]([CH3:1])[CH:15]=[C:5]3[N:6]=[C:7]([CH3:14])[CH:8]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 18406994N-(2,5-Dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl)-ethane-1,2-diamine

Product 1

HCID 18406983N-Cyclopentyl-N'-(2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl)-ethane-1,2-diamineYield 128%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-yl)-ethane-1,2-diamine (3.2 g, 16 mmol) and cyclopentanone (2.7 mL, 30 mmol) in methanol (30 mL)/acetic acid (3 mL) was added sodium cyanoborohydride (0.94 g, 15 mmol), portionwise. After stirring 1 hour the reaction was concentrated under reduced pressure and then extracted from saturated aqueous sodium bicarbonate with ethyl acetate. The combined extracts were dried (Na2SO4), concentrated under reduced pressure to give the crude product as a brown oil (5.6 g): +APcI MS (M+1)+ 274; 1H NMR (CDCl3) δ: 6.11 (s, 1H), 6.76 (s, 1H), 3.21 (t, 2H), 3.21 (m, 1H ), 3.04 (t, 1H), 2.42 (s, 3H), 2.40 (s, 3H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted from saturated aqueous sodium bicarbonate with ethyl acetate
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8ed2137a1d3476e96029ff70a44a0bb
Source dataset
uspto-grants-2002_11
Patent number
US06476038B1

Reaction notes

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