Water → HCID 21070628, compound

HRID 1435240Notes

Reaction equation

HRID 1435240 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4](S(C)=O)[N:3]=1.[O:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1.O>CN1CCCC1=O>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:28][CH:25]2[CH2:26][CH2:27][O:22][CH2:23][CH2:24]2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4192234-AminotetrahydropyranHCID 21070605HCID 21070605, compound

Product 1

HCID 21070628HCID 21070628, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of (4-amino-2-methanesulfinyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanone (235 mg, 0.73 mmol, Example 157) and tetrahydro-pyran-4-ylamine (Combi-Blocks) (260 mg, 2.3 mmol) in N-methylpyrrolidinone (15 ml) was heated for 30 minutes at 100° C. The solution was cooled, poured into water and extracted into ethyl acetate (2×). The combined organic extracts were washed with 5% sodium bicarbonate and saturated sodium chloride. The solution was dried (Na2SO4) and solvent was removed under vacuum to give a crude solid. Purification was by silica gel chromatography to give [4-amino-2-(tetrahydro-pyran-4-ylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid. HRMS, observed: 346.1445; Calcd for M+: 346.1441.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted into ethyl acetate (2×)
  3. washThe combined organic extracts were washed with 5% sodium bicarbonate and saturated sodium chloride
  4. dry with materialThe solution was dried (Na2SO4) and solvent
  5. customwas removed under vacuum
  6. customto give a crude solid
  7. customPurification

Sources & evidence

ORD record
ord-48bf8a8bb24c48c8b49b67e10efc9653
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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