Pyrrolidine → HCID 86267821, compound

HRID 709997Notes

Reaction equation

HRID 709997 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:5][N:4]=[C:3]1SC.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:5][N:4]=[C:3]1[N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 90416241HCID 90416241, compound

Product 1

HCID 86267821HCID 86267821, compoundYield 67.5%

Procedure

A solution of Example C3 (0.087 g, 0.207 mmol) in pyrrolidine (1.75 mL, 21.31 mmol) was heated at 100° C. in a sealed vessel overnight, cooled to RT, concentrated to dryness and purified via silica gel chromatography (EtOAc, MeOH/DCM). The material was treated with MeCN, sonicated and the resulting solid collected via filtration and dried to afford 3-methyl-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(pyrrolidin-1-yl)pyrimidin-4(3H)-one (62 mg, 67%). 1H NMR (400 MHz, DMSO-d6): δ 8.65 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 8.30 (d, J=8.6 Hz, 1H), 8.25 (s, 1H), 7.96 (s, 1H), 7.54 (d, J=8.6 Hz, 1H), 7.24 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.84 (s, 3H), 3.58 (m, 4H), 3.45 (s, 3H), 2.35 (s, 3H), 1.87 (m, 4H); MS (ESI) m/z: 444.2 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. custompurified via silica gel chromatography (EtOAc, MeOH/DCM)
  3. additionThe material was treated with MeCN
  4. customsonicated
  5. filtrationthe resulting solid collected via filtration
  6. customdried

Sources & evidence

ORD record
ord-adad75d57ba542408abf7083781fd618
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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