Hydrochloric Acid → 4-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 527876Notes

Reaction equation

HRID 527876 reaction equation
C(OC([N:8]1[CH2:15][CH2:14][N:13]([C:16]2[C:17]3[CH:24]=[CH:23][NH:22][C:18]=3[N:19]=[CH:20][N:21]=2)[CH2:12][C:9]21[CH2:11][CH2:10]2)=O)(C)(C)C.Cl>C(OCC)C.O1CCOCC1>[CH2:11]1[C:9]2([CH2:12][N:13]([C:16]3[C:17]4[CH:24]=[CH:23][NH:22][C:18]=4[N:19]=[CH:20][N:21]=3)[CH2:14][CH2:15][NH:8]2)[CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 574772807-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carboxylic acid tert-butyl ester2×

Product 1

HCID 668882444-(4,7-Diaza-spiro[2.5]oct-7-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To 7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carboxylic acid tert-butyl ester (intermediate 1) (0.5 g, mmol) dissolved in diethyl ether (20 ml) was added HCl in dioxane (ml, M) and the reaction mixture was stirred for 5 hours at room temperature. The precipitate was isolated by filtration, and washed with diethyl ether (2×5 ml). The precipitate was suspended in THF (50 ml) and stirred vigorously with K2CO3 (5 gram) for 3 hours. After filtration and evaporation of the solvent in vacuo, the product was obtained as an off-white compound.

Workup

  1. customThe precipitate was isolated by filtration
  2. washwashed with diethyl ether (2×5 ml)
  3. stirringstirred vigorously with K2CO3 (5 gram) for 3 hours
  4. filtrationAfter filtration and evaporation of the solvent in vacuo
  5. customthe product was obtained as an off-white compound

Sources & evidence

ORD record
ord-301d977b7c69416883eecb8da2249619
Source dataset
uspto-grants-2016_05
Patent number
US09346809B2

Reaction notes

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