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

HRID 981531Notes

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]

Participants

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

temperatureThe mixed solution was warmed
filtrationsubjected to filtration
customThe filtrate was purified over a chromatographic column
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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