Water → [4-Amino-2-(4-hydroxy-cyclohexylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

HRID 1371652Notes

Reaction equation

HRID 1371652 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.C(=O)(O)[O-].[Na+].[NH2:15][C:16]1[C:21]([C:22]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[O:31][CH3:32])=[O:23])=[CH:20][N:19]=[C:18](S(CC)(=O)=O)[N:17]=1.O>CN(C)C=O>[NH2:15][C:16]1[C:21]([C:22]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[O:31][CH3:32])=[O:23])=[CH:20][N:19]=[C:18]([NH:2][CH:3]2[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]2)[N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10472348(4-Amino-2-ethanesulfonyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanoneHCID 178479278HCID 178479278, compound

Product 1

HCID 21070549[4-Amino-2-(4-hydroxy-cyclohexylamino)-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of trans-4-amino-cyclohexanol hydrochloride (108 mg, 0.71 mmol, Aldrich) in dimethylformamide, were added sodium bicarbonate(98 mg, 0.92 mmol) and (4-amino-2-ethanesulfonyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanone (201 mg, 0.59 mmol, Example 48) and the mixture was stirred at 90° C. for 1 hour. The mixture was poured into water and extracted with ethyl acetate. The extracts were dried with sodium sulfate and concentrated. The residue was chromatographed (2.5% methanol in dichloromethane) to give a white solid. 172 mg, 81%. MS(ES) (M+H)+=361.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts were dried with sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed (2.5% methanol in dichloromethane)
  5. customto give a white solid

Sources & evidence

ORD record
ord-8da22e31415442f1a1c7018192e884aa
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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