Methyl chloroformate → HCID 11503063, compound

HRID 1091403Notes

Reaction equation

HRID 1091403 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[O:18][CH2:17][CH2:16][N:15]([C:19]3[N:24]([CH3:25])[C:23](=[O:26])[CH:22]=[C:21]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][C:28]=4[F:33])[N:20]=3)[CH2:14]2)=[CH:9][CH:8]=1.C(N(CC)CC)C>O1CCCC1>[F:33][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][C:27]=1[C:21]1[N:20]=[C:19]([N:15]2[CH2:16][CH2:17][O:18][C@@H:13]([C:10]3[CH:11]=[CH:12][C:7]([NH:6][C:2](=[O:3])[O:4][CH3:5])=[CH:8][CH:9]=3)[CH2:14]2)[N:24]([CH3:25])[C:23](=[O:26])[CH:22]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 11494661HCID 11494661, compound

Product 1

HCID 11503063HCID 11503063, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl chloroformate (0.13 g, 1.38 mmol) was added to a solution of 2-((2S)-2-(4-aminophenyl)morpholine-4-yl)-6-(3-fluoropyridin-4-yl)-3-methyl-3H-pyrimidin-4-one obtained in Example 13 (0.35 g, 0.92 mmol) and triethylamine (0.25 g, 2.47 mmol) in tetrahydrofuran (20 ml) and the solution was stirred at room temperature for one hour. 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 methyl (4-((2S)-4-(6-(3-fluoropyridin-4-yl)-3-methyl-4-oxo-3H-pyrimidin-2-yl)morpholin-2-yl)phenyl)carbamate (0.17 g, 42%) 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-760f2986686d42e2b3b261012bd44815
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

Loading…