Hydrochloric Acid → 3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde

HRID 2386384Notes

Reaction equation

HRID 2386384 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1.Cl>CC#N>[OH:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][NH:16][C:12]2[N:11]=[C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[CH:3]=[O:2])[CH:15]=[CH:14][N:13]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670450574-{2-[4-(3-Dimethoxymethyl-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Product 1

HCID 866032623-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Intermediate 27 (2.2 g) was treated with 30 mL of 3N HCl in 60 mL of CH3CN at room temperature overnight. The solvent was removed by rotary evaporation and the residue partitioned between ethyl acetate/sat. NaHCO3. Yield: 1.9 g, 99%. LC-MS showed the product had the expected M+H+ of 320.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue partitioned between ethyl acetate/

Sources & evidence

ORD record
ord-6a1676b8fec94dc09692ea89beb89725
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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