Sodium hydride → HCID 67586854, compound

HRID 1416643Notes

Reaction equation

HRID 1416643 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].[H-].[Na+].Br[C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.[Cl-:18].[Na+].O>CN(C=O)C>[ClH:18].[ClH:18].[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 783445-BromopyrimidineHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 57417360Sodium chloride; water

Product 1

HCID 67586854HCID 67586854, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a sample of 1-methyl-2(S)-pyrrolidinemethanol (Aldrich, 16.81 mmol) in 2 mL of DMF was added 0.74 g of NaH (60% dispersion in oil, 18.49 mmol) and 2.68 g (16.81 mmol) of 5-bromopyrimidine. The reaction mixture was stirred at 60° C. for 18 hours, then poured onto ice. The mixture was diluted with brine, and extracted with methylene chloride. The extract was dried over MgSO4, and the solvent was removed. The residue was chromatographed on silica gel, eluting with 20:1 chloroform:methanol. The compound was then taken up in methylene chloride, HCl in ether was added, and the volatiles removed under vacuum. The salt was recrystallized from acetonitrile/ether to afford 822 mg of the title compound. mp >160° C. (dec). MS (DCI/NH3) m/e: 194 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.88 (s, 1H-), 8.65 (s, 2H), 4.64 (dd, J=11.2, 3.1 Hz, 1H), 4.47 (m, 1H), 3.95 (m, 1H), 3.77 (m, 1H), 3.29 (m, 1H), 3.05 (s, 3H), 2.43 (m, 1H), 2.24 (m, 1H), 2.11 (m, 2H). Anal. Calc. for C10H15N3OCl2 : C, 45.13; H, 6.44; N, 15.79; Found C, 45.13; H, 6.74; N, 15.69. [α]25D =-2.6° (c=0.57, methanol).

Workup

  1. additionpoured onto ice
  2. extractionextracted with methylene chloride
  3. dry with materialThe extract was dried over MgSO4
  4. customthe solvent was removed
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 20:1 chloroform
  7. additionwas added
  8. customthe volatiles removed under vacuum
  9. customThe salt was recrystallized from acetonitrile/ether

Sources & evidence

ORD record
ord-c131d03aea604d458ce7e684fa66a88f
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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