(R)-3-Pyrrolidinol → HCID 57974226, compound

HRID 1362877Notes

Reaction equation

HRID 1362877 reaction equation
[CH3:1][C:2]1[C:3]([NH:22][C:23]2[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=2[C:25](OCC)=[O:26])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH:10]=2)=[N:6][CH:7]=1.[NH:34]1[CH2:38][CH2:37][C@@H:36]([OH:39])[CH2:35]1>>[CH3:1][C:2]1[C:3]([NH:22][C:23]2[CH:33]=[CH:32][CH:31]=[CH:30][C:24]=2[C:25]([N:34]2[CH2:38][CH2:37][C@@H:36]([OH:39])[CH2:35]2)=[O:26])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]3)[CH:10]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 57974139HCID 57974139, compound

Product 1

HCID 57974226HCID 57974226, compound

Conditions

Temperature
125 °C

Procedure

Ethyl 2-[(5-methyl-2-{[3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)amino]benzoate (120 mg, 0.27 mmol) and (R)-(+)-3-pyrrolidinol (0.65 mL, used as solvent) were combined in a vessel, which was sealed and heated with stirring at 125° C. for 18 h. The reaction was cooled to room temperature and evaporated. The residue was partitioned between ethyl acetate (10 mL) and water (10 mL). The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified using normal phase HPLC eluting with a gradient of dichloromethane/methanol/ammonium hydroxide (90:10:0-90:10:1) affording the title compound as an off-white solid; yield 63 mg. (48%). (MS: M(C27H33N7O2)=487.60, (M+H)+=488.2.

Workup

  1. customwhich was sealed
  2. temperatureheated
  3. temperatureThe reaction was cooled to room temperature
  4. customevaporated
  5. customThe residue was partitioned between ethyl acetate (10 mL) and water (10 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified
  11. washeluting with a gradient of dichloromethane/methanol/ammonium hydroxide (90:10:0-90:10:1)

Sources & evidence

ORD record
ord-ad5ebb20d1e14ced8dabe69f74d5f1de
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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