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3-Pentanol → HCID 86606453, compound

HRID 1811576
Notes
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Reaction equation

HRID 1811576 reaction equation
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].N1([C:12](N2C=CN=C2)=[O:13])C=CN=C1.CCN(C(C)C)C(C)C.Cl.[Cl:29][C:30]1[C:35]([O:36][CH3:37])=[C:34]([O:38][CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[N:33]=[CH:32][N:31]=1>C1COCC1>[CH2:2]([CH:3]([O:6][C:12]([N:42]1[CH2:43][CH2:44][CH:39]([O:38][C:34]2[C:35]([O:36][CH3:37])=[C:30]([Cl:29])[N:31]=[CH:32][N:33]=2)[CH2:40][CH2:41]1)=[O:13])[CH2:4][CH3:5])[CH3:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 114283-PentanolHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 86606454HCID 86606454, compound

Product 1

HCID 86606453HCID 86606453, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

Pentan-3-ol (0.88 g, 9.99 mmol) and di-imidazol-1-yl-methanone (1.39, 8.57 mmol) were added to THF (10 mL) and stirred at 50° C. for one hour. DIPEA (1.38 g, 10.7 mmol) and 4-chloro-5-methoxy-6-(piperidin-4-yloxy)-pyrimidine HCl (2.00 g, 7.14 mmol) were added, the vessel sealed and heated by microwave at 150° C. for one hour. Upon cooling the reaction mixture was partitioned between water and Ethyl Acetate, the organic phase washed with brine and dried with Sodium Sulfate. The crude material was purified by column chromatograph (silica gel) with 10-30% EtOAc/Hexanes to yield 1.0 grams (39%) of the desired product, as a white solid. 1HNMR (CDCl3, 400 MHz) δ 0.91 (t, J=7.83 Hz, 6H), 1.55-1.63 (m, 4H), 1.78-1.88 (m, 2H), 1.99-2.08 (m, 2H), 3.39-3.46 (m, 2H), 3.78-3.85 (m, 2H), 3.92 (s, 3H), 4.67 (m, 1H), 5.36-5.43 (m, 1H), 8.26 (s, 1H). Exact mass calculated for C16H24ClN3O4: 357.15. found: 358.3 (MH+).

Workup

  1. customthe vessel sealed
  2. temperatureheated by microwave at 150° C. for one hour
  3. temperatureUpon cooling the reaction mixture
  4. customwas partitioned between water and Ethyl Acetate
  5. washthe organic phase washed with brine
  6. dry with materialdried with Sodium Sulfate
  7. customThe crude material was purified by column chromatograph (silica gel) with 10-30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-7aa55d639b724b52ad9778f5f1a71388
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362248B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes