4-Aminotetrahydropyran → HCID 71727365, compound

HRID 2365832Notes

Reaction equation

HRID 2365832 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.[CH:8]([N:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][N:30]=[C:29](S(C)(=O)=O)[N:28]=2)=[CH:23][C:22]1=[O:37])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CC(N(C)C)=O.O>[CH:8]([N:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][N:30]=[C:29]([NH:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[N:28]=2)=[CH:23][C:22]1=[O:37])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 4192234-AminotetrahydropyranHCID 89784761HCID 89784761, compound

Product 1

HCID 71727365HCID 71727365, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

Tetrahydro-2H-pyran-4-amine (0.20 g, 2.0 mmol) was added to 1-benzhydryl-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-one (0.12 g, 0.29 mmol) in DMA (3 mL) in a microwave vial. The mixture was heated at 120° C. for 1 hour in a microwave. The reaction mixture was diluted with water and extracted with EtOAc. The EtOAc was washed with water, twice with brine, dried over MgSO4, filtered, and evaporated to yield a crude product (0.09 g) as a film. This was chromatographed on a 10 g Biotage SNAP column with EtOAc. Fractions 9-20 contained a film (0.0764 g). This was triturated with water, dried, then triturated with hexane and dried to afford the desired 1-benzhydryl-4-(2-((tetrahydro-2H-pyran-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.072 g, 0.16 mmol, 57% yield) as a film. 1H NMR (400 MHz, CDCl3) δ 8.38 (d, 1H), 7.52 (s, 1H), 7.40-7.15 (m, 9H), 6.91 (d, 1H), 6.76-6.72 (m, 1H), 5.25-5.21 (m, 1H), 4.15-4.06 (m, 1H), 4.02-3.96 (m, 2H), 3.59-3.51 (m, 2H), 2.09-2.03 (m, 2H), 1.62-1.52 (m, 2H); m/z (APCI-pos) M+1=439.2.

Workup

  1. extractionextracted with EtOAc
  2. washThe EtOAc was washed with water, twice with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a crude product (0.09 g) as a film
  7. customThis was chromatographed on a 10 g Biotage SNAP column with EtOAc
  8. customThis was triturated with water
  9. customdried
  10. customtriturated with hexane
  11. customdried

Sources & evidence

ORD record
ord-d931de2abb6e42d6b3370441148e7277
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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