Diisopropylethylamine → HCID 178461963, compound

HRID 626303Notes

Reaction equation

HRID 626303 reaction equation
[NH2:1][C@H:2]([C:4]1[O:5][C:6]2[C:11]([C:12](=[O:20])[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:10][C:9]([Br:21])=[CH:8][CH:7]=2)[CH3:3].C(N(CC)C(C)C)(C)C.Br[C:32]1[N:40]=[CH:39][N:38]=[C:37]2[C:33]=1[NH:34][CH:35]=[N:36]2>C(O)(C)(C)C>[N:40]1[C:32]([NH:1][C@H:2]([C:4]2[O:5][C:6]3[C:11]([C:12](=[O:20])[C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:9]([Br:21])=[CH:8][CH:7]=3)[CH3:3])=[C:33]2[C:37]([NH:36][CH:35]=[N:34]2)=[N:38][CH:39]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5287830Purine, 6-bromo-HCID 53234447HCID 53234447, compound

Product 1

HCID 178461963HCID 178461963, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

This example is also described in Example 24 of WO 2011/055215. To a solution of (S)-2-(1-aminoethyl)-6-bromo-3-phenyl-4H-chromen-4-one (0.20 g, 0.581 mmoles) in tert-butanol (6 ml), N,N-diisopropylethyl amine (0.2 ml, 1.162 mmoles) and 6-bromopurine (0.087 g, 0.435 mmoles) are added and refluxed for 24 h. The reaction mixture is concentrated, diluted with water, extracted with ethyl acetate. The organic layer is dried over sodium sulphate and concentrated under reduced pressure. The crude product is purified by column chromatography with methanol:ethyl acetate to afford the title compound as yellow solid. MP: 151-154° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 12.94 (s, 1H), 8.09 (br s, 3H), 7.94 (d, J=7.9 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 7.42 (m, 6H), 5.22 (br t, 1H), 1.82 (d, J=6.4 Hz, 3H). Mass: 463.99 (M+1).

Workup

  1. temperaturerefluxed for 24 h
  2. concentrationThe reaction mixture is concentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by column chromatography with methanol

Sources & evidence

ORD record
ord-1d99e43ddc554aa397a081b850bea0e5
Source dataset
uspto-grants-2016_04
Patent number
US09309216B2

Reaction notes

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