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Ethanol → 8-tert-Butyl-6,7-dihydropyrrolo(3,2-e)-5-methylpyrazolo(1,5-a)pyrimidine-3-carbonitrile

HRID 981531
Notes
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Reaction equation

HRID 981531 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9](C)[C:10]([C:11]#[N:12])=[C:6]2[N:5]=[C:4]([CH3:14])[C:3]=1[CH2:15][CH2:16]Cl.C(N(CC)CC)C.[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26].C(O)C>C(C(C)=O)C>[C:25]([N:29]1[C:2]2[N:7]3[N:8]=[CH:9][C:10]([C:11]#[N:12])=[C:6]3[N:5]=[C:4]([CH3:14])[C:3]=2[CH2:15][CH2:16]1)([CH3:28])([CH3:27])[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 15729005HCID 15729005, compound

Product 1

HCID 1884028-tert-Butyl-6,7-dihydropyrrolo(3,2-e)-5-methylpyrazolo(1,5-a)pyrimidine-3-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent

Conditions

Temperature
85 °C

Procedure

(ii-1) 2.7 g (0.01 mol) of Compound (VI) [R2 =CH3, R3 =CN], 2 ml of triethylamine, 3.2 ml of tert-butylamine, and 15 ml of anhydrous ethanol were placed in a closed tube and heated at 85° C. in a water bath for 8 hours. Then the tube was opened, and 100 ml of methyl ethyl ketone was added to the reaction solution. The mixed solution was warmed and subjected to filtration. The filtrate was purified over a chromatographic column packed with 10 g of silica gel (pH=7, 200 mesh) using methyl ethyl ketone in advance. The eluant was then evaporated to obtain 2.4 g of 8-tert-butyl-3-cyano-6,7-dihydro-2,5-dimethyl-8H-pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidine [R1 =C(CH3)3, R2 =CH3, R3 =CN in formula (I)] (Compound 2 of this invention) as yellowish orange plate crystals having a melting point of 229°-230° C. at a yield of 80.0%.

Workup

  1. temperatureThe mixed solution was warmed
  2. filtrationsubjected to filtration
  3. customThe filtrate was purified over a chromatographic column
  4. customThe eluant was then evaporated

Sources & evidence

ORD record
ord-56555f7ff36041dabf3b0ce007838139
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04992442

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes