Ammonia → 3',4'-Dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indol]-8'-amine

HRID 853889Notes

Reaction equation

HRID 853889 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][NH2:14])[C:6](=O)[C:5]12[O:20][CH2:19][CH2:18][CH2:17][O:16]1.N.C1COCC1>CCOC(C)=O>[N:14]1[CH2:13][CH2:12][CH2:11][N:7]2[C:8]3[CH:9]=[CH:10][C:2]([NH2:1])=[CH:3][C:4]=3[C:5]3([O:20][CH2:19][CH2:18][CH2:17][O:16]3)[C:6]=12

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 589325815'-Amino-1'-(3-aminopropyl)spiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one

Product 1

HCID 116804673',4'-Dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indol]-8'-amineYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5′-Amino-1′-(3-aminopropyl)spiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one (1.56 g, 5.63 mmol) was dissolved in 2M EtOAc.NH3 (1.90 mL) and THF (10 mL) and heated in a steel pressure vessel at 135° C. for 16 hr. The reaction mixture was cooled to room temperature and combined with silica gel and concentrated. The adsorbate was purified on Biotage KP silica gel eluting with a step gradient of CH2Cl2/CH3OH/NH4OH (95/3/2) to (85/10/5) to give the title compound as a bright yellow-orange solid (1.11 g, 76% yield). NMR (300 Mz, DMSO-d6): consistent.

Workup

  1. concentrationconcentrated
  2. customThe adsorbate was purified on Biotage KP silica gel eluting with a step gradient of CH2Cl2/CH3OH/NH4OH (95/3/2) to (85/10/5)

Sources & evidence

ORD record
ord-2081b6098b8045b8a929601dbb4a7ff0
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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