Diisopropylethylamine → HCID 67969064, compound

HRID 2362329Notes

Reaction equation

HRID 2362329 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][C:13]3[N:22]=[C:21]([CH3:23])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[C:6]3=[N:24][CH2:25][CH2:26][N:5]3[C:4]=2[N:3]=1.CCN(C(C)C)C(C)C.Br[CH2:37][C:38]#[C:39][CH3:40]>CN(C=O)C>[Br:1][C:2]1[N:10]([CH2:37][C:38]#[C:39][CH3:40])[C:9]2[C:8](=[O:11])[N:7]([CH2:12][C:13]3[N:22]=[C:21]([CH3:23])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[C:6]3=[N:24][CH2:25][CH2:26][N:5]3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27568621-Bromo-2-butyne2×HCID 67960573HCID 67960573, compound

Product 1

HCID 67969064HCID 67969064, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-bromo-5-((4-methylquinazolin-2-yl)methyl)-7,8-dihydro-3H-imidazo[2,1-b]purin-4(5H)-one 15 (470 mg, 1.14 mmol) in DMF (5 ml) was added Hunig's base (0.3 ml, 1.71 mmol) and 1-bromo-2-butyne (0.145 ml, 1.6 mmol) at room temperature. The mixture was stirred over night. Another 0.103 ml (1.14 mmol) of 1-bromo-2-butyne was added and stirred over night. The reaction was extracted by DCM twice, washed with NaHCO3 and brine, dried (MgSO4) and concentrated. The crude product was purified by flash chromatography (MeOH/DCM) to afford 2-bromo-3-(but-2-ynyl)-5-((4-methylquinazolin-2-yl)methyl)-7,8-dihydro-3H-imidazo[2,1-b]purin-4(5H)-one 16. 1H NMR S 8.02 (d, J=7.81, 1H), 7.90 (d, J=7.81, 1H), 7.78 (t, J=8.59, 1H), 7.54 (t, J=8.59, 1H), 5.50 (s, 2H), 5.30 (s, 2H), 5.08 (q, J=2.34, 21-1), 4.12 (t, J=9.38, 2H), 3.92 (t, 0.1=9.38, 2H), 2.89 (s, 3H), 1.79 (t, J=2.34, 3H).

Workup

  1. stirringstirred over night
  2. extractionThe reaction was extracted by DCM twice
  3. washwashed with NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-6d256261c181498a9bd4c0acf9e2a7e7
Source dataset
uspto-grants-2014_04
Patent number
US08691832B2

Reaction notes

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