Chloroacetaldehyde → HCID 178518393, compound

HRID 2046989Notes

Reaction equation

HRID 2046989 reaction equation
Cl[C:2]1[C:3]([NH:32]C2C=CC=CC=2S(C(C)C)(=O)=O)=[N:4][C:5](NC2C(OC(C)C)=CC(C3CCN(C(=O)CN(C)C)CC3)=C(C)C=2)=[N:6][CH:7]=1.[CH3:45][C:46]([O-:48])=O.[Na+].ClCC=[O:53].Cl>O>[N:4]1[C:5]2[NH:6][CH:7]=[CH:2][C:45]=2[C:46]([OH:48])=[N:32][C:3]=1[OH:53]

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 582908721-(4-(4-(5-Chloro-4-(2-(isopropylsulfonyl)phenylamino)pyrimidin-2-ylamino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)-2-(dimethylamino)ethanone

Product 1

HCID 178518393HCID 178518393, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 40 g 6-aminopyrimidine-2,4-diol (1) (315 mmol) in 1.0 L of water was added 54.3 g NaOAc (662 mmol) and 48 mL of 2-chloroacetaldehyde (50 wt % in H2O, 378 mmol). The resulting mixture was heated to reflux and stirred for three hours. The reaction mixture was cooled to room temperature followed by slow addition of 300 mL of 2N HCl in H2O. The precipitate was filtered, washed with H2O and dried at 50° C. under vacuum to give the title compound.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. filtrationThe precipitate was filtered
  4. washwashed with H2O
  5. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-d44233131ca048a19e138cd06aeaf538
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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