Diisopropylethylamine → HCID 72944224, compound

HRID 1505701Notes

Reaction equation

HRID 1505701 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][N:16]1[CH:20]=[C:19]([C:21]2[CH:22]=[C:23]([C:27]3[N:32]=[CH:31][C:30]([C:33]4[CH:34]=[N:35][N:36]([CH:38]5[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]5)[CH:37]=4)=[CH:29][N:28]=3)[CH:24]=[CH:25][CH:26]=2)[CH:18]=[N:17]1.CCN(C(C)C)C(C)C.[O:53]1[CH2:56][C:55](=O)[CH2:54]1>ClCCCl>[CH3:15][N:16]1[CH:20]=[C:19]([C:21]2[CH:22]=[C:23]([C:27]3[N:28]=[CH:29][C:30]([C:33]4[CH:34]=[N:35][N:36]([CH:38]5[CH2:43][CH2:42][N:41]([CH:55]6[CH2:56][O:53][CH2:54]6)[CH2:40][CH2:39]5)[CH:37]=4)=[CH:31][N:32]=3)[CH:24]=[CH:25][CH:26]=2)[CH:18]=[N:17]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 89924163HCID 89924163, compound

Product 1

HCID 72944224HCID 72944224, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Sodium triacetoxyborohydride (0.13 g; 0.62 mmol; 2.0 eq.) was slowly added to a solution of 2-[3-(1-methyl-1H-pyrazol-4-yl)phenyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)pyrimidine (example 1,200 mg; 0.31 mmol; 1.0 eq.), DIEA (53 μl; 0.31 mmol; 1.0 eq.) and 3-oxetanone (39 μl; 0.62 mmol; 2.0 eq.) in DCE (4 mL). The reaction mixture was then stirred at 50° C. for 3 h. It was then quenched by addition of water. Aqueous phase was basified to pH 12 and extracted with EtOAc (three times). Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a beige powder (100 mg, 73%). 1H NMR (300 MHz, DMSO-d6) δ 9.17 (s, 2H), 8.59-8.50 (m, 2H), 8.27 (s, 1H), 8.25-8.18 (m, 1H), 8.18-8.11 (m, 1H), 7.96-7.89 (m, 1H), 7.77-7.66 (m, 1H), 7.52 (t, J=7.7 Hz, 1H), 4.56 (t, J=6.5 Hz, 2H), 4.46 (t, J=6.1 Hz, 2H), 4.23 (s, 1H), 3.90 (s, 3H), 3.51-3.40 (m, 1H), 2.87-2.73 (m, 2H), 2.17-1.90 (m, 6H). HPLC (Condition A): Rt 2.49 min (purity 97.2%). MS (ESI+): 442.5.

Workup

  1. customIt was then quenched by addition of water
  2. extractionextracted with EtOAc (three times)
  3. washCombined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ea1598cf80f493398e3aeaa6d67f5be
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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