Ammonium Hydroxide → HCID 11536030, compound

HRID 853893Notes

Reaction equation

HRID 853893 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:21][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([C:19]#[N:20])=[CH:11][C:12]=3[C:13]3(OCCC[O:14]3)[C:5]2=[N:4][CH2:3]1.[NH4+].[OH-]>CS(O)(=O)=O>[CH3:1][C:2]1([CH3:22])[CH2:21][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([C:19]#[N:20])=[CH:11][C:12]=3[C:13](=[O:14])[C:5]2=[N:4][CH2:3]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 11580242HCID 11580242, compound

Product 1

HCID 11536030HCID 11536030, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

At room temperature a solution containing 3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indole]-8′-carbonitrile in methanesulfonic acid was stirred for 1.5 h. The reaction was poured carefully onto crushed ice (100 mL), basified with concentrated NH4OH and extracted with CH2Cl2. The combined organic extracts were washed with H2O (1×), dried (Na2SO4) and purified on Biotage KP-Sil eluting with 40% acetone/hexane to give 0.119 g (94%) of the title compound as a yellow solid. Anal. Calc'd. for C14H13N3O 0.2H2O: C; 69.23; H, 5.56; N, 17.30. Found: C, 69.59; H, 5.44; N, 17.05. NMR (400 Mz, DMSO-d6): consistent. MS: (ES+) m/z 240 [M+H, 100]. m.p.: 178-184° C.

Workup

  1. additionThe reaction was poured carefully
  2. extractionextracted with CH2Cl2
  3. washThe combined organic extracts were washed with H2O (1×)
  4. dry with materialdried (Na2SO4)
  5. custompurified on Biotage KP-Sil
  6. washeluting with 40% acetone/hexane

Sources & evidence

ORD record
ord-1218b0b7228e4a748143d5e08994d3ba
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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