Triethylamine → HCID 66594863, compound

HRID 1091402Notes

Reaction equation

HRID 1091402 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[F:16])[N:3]=1.Cl.[CH3:18][N:19]([C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]2[O:36][CH2:35][CH2:34][NH:33][CH2:32]2)=[CH:27][CH:26]=1)[C@@H:20]1[CH2:24][CH2:23][O:22][CH2:21]1.C(N(CC)CC)C>O1CCCC1>[F:16][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[C:4]1[N:3]=[C:2]([N:33]2[CH2:34][CH2:35][O:36][C@@H:31]([C:28]3[CH:27]=[CH:26][C:25]([N:19]([CH3:18])[C@@H:20]4[CH2:24][CH2:23][O:22][CH2:21]4)=[CH:30][CH:29]=3)[CH2:32]2)[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 595768122-Chloro-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-oneHCID 66594538HCID 66594538, compound

Product 1

HCID 66594863HCID 66594863, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-one (0.26 g, 1.09 mmol) was added to a solution of (2S)-2-(4-(N-methyl-N-((3R)-tetrahydrofuran-3yl)amino)phenyl)morpholine hydrochloride obtained in Reference Example 6 (0.4 g, 1.19 mmol) and triethylamine (0.6 g, 5.93 mmol) in tetrahydrofuran (20 ml) at room temperature for 15 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting 5-10% methanol in chloroform to furnish 6-(3-fluoropyridin-4-yl)-2-((2S)-2-(4-(N-methyl-N-((3R)-tetrahydrofuran-3-yl)amino)-phenyl)morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.20 g, 39%) as white crystals.

Workup

  1. customThe mixture was partitioned between water and chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record
ord-7758a9928ab24ce8993ed668d77685d2
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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