2-(Dimethylamino)ethanol → 4'-(2-(dimethylamino)ethoxy)-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

HRID 2059757Notes

Reaction equation

HRID 2059757 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].CC(C)([O-])C.[K+].Cl[C:14]1[C:23]2[CH2:22][CH2:21][CH2:20][C:19]3([CH2:27][CH2:26][CH2:25][CH2:24]3)[C:18]=2[N:17]=[C:16]([NH2:28])[N:15]=1>C1COCC1.C(Cl)Cl.O>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:14]1[C:23]2[CH2:22][CH2:21][CH2:20][C:19]3([CH2:27][CH2:26][CH2:25][CH2:24]3)[C:18]=2[N:17]=[C:16]([NH2:28])[N:15]=1

Participants

7

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 23665647Potassium tert-butoxideHCID 866343344'-chloro-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

Product 1

HCID 442316234'-(2-(dimethylamino)ethoxy)-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(dimethylamino)ethanol (63.9 μL, 0.631 mmol) in THF (5 mL) was treated with potassium tert-butoxide (78 mg, 0.694 mmol) at 0° C., and the reaction mixture was stirred for 30 minutes at ambient temperature. It was then treated with a solution of the product from Example 14A (30 mg, 0.126 mmol) in THF (2 mL) at ambient temperature, and the whole was stirred for 2 hours. The mixture was diluted with CH2Cl2 (20 mL) and H2O (10 mL), then the organic layer was separated, dried with MgSO4, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel, eluting with NH4OH/MeOH/CH2Cl2 (0.8/7.2/92), to afford the title product. 1H NMR (300 MHz, CDCl3) δ 4.56 (s, 2 H), 4.37 (t, 2 H), 2.68 (t, J=5.93 Hz, 2 H), 2.43 (t, J=6.10 Hz, 2 H), 2.32 (s, 6 H), 2.01-2.13 (m, 2 H), 1.79-1.90 (m, 2 H), 1.59-1.74 (m, 6 H), 1.47-1.57 (m, 2 H). MS (DCI+) m/z 291 (M+H).

Workup

  1. stirringthe whole was stirred for 2 hours
  2. customthe organic layer was separated
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was chromatographed on silica gel
  6. washeluting with NH4OH/MeOH/CH2Cl2 (0.8/7.2/92)

Sources & evidence

ORD record
ord-ea9d51671ce94fe7b7d19a4ef5d53832
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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