Triethylamine → 3-Chloro-1-(2,2-dimethyl-morpholin-4-yl)-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b,9-tetraaza-fluorene

HRID 334162Notes

Reaction equation

HRID 334162 reaction equation
Cl[C:2]1[C:14]2[N:13]=[C:12]3[N:7]([CH2:8][CH2:9][O:10][C:11]3([CH3:16])[CH3:15])[C:6]=2[N:5]=[C:4]([Cl:17])[N:3]=1.[CH3:18][C:19]1([CH3:25])[O:24][CH2:23][CH2:22][NH:21][CH2:20]1.C(N(CC)CC)C>>[Cl:17][C:4]1[N:3]=[C:2]([N:21]2[CH2:22][CH2:23][O:24][C:19]([CH3:25])([CH3:18])[CH2:20]2)[C:14]2[N:13]=[C:12]3[N:7]([C:6]=2[N:5]=1)[CH2:8][CH2:9][O:10][C:11]3([CH3:16])[CH3:15]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 189596742,2-DimethylmorpholineHCID 866673712,4-Dichloro-6,6-dimethyl-8,9-dihydro-6H-[1,4]oxazino[4,3-e]purine

Product 1

HCID 866673733-Chloro-1-(2,2-dimethyl-morpholin-4-yl)-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b,9-tetraaza-fluoreneYield 85.4%

Conditions

Temperature
140 °C

Procedure

A mixture of 1,3-dichloro-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b,9-tetraaza-fluorene (100 mg, 0.366 mmol), 2,2-dimethyl-morpholine (84 mg, 0.732 mmol) and triethylamine (77 μL, 0.55 mmol) in IMS (2 mL) was heated at 140° C. for 20 mins in a microwave reactor, then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, 10% ethyl acetate in cyclohexane) affording 3-Chloro-1-(2,2-dimethyl-morpholin-4-yl)-8,8-dimethyl-5,6-dihydro-8H-7-oxa-2,4,4b,9-tetraaza-fluorene as a white solid (110 mg, 85%). LCMS (method A): RT=3.51 min, [M+H]+=352.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, 10% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-99013a31539c4c7aa296464e38953986
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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