Hydrochloric Acid → HCID 18694187, compound

HRID 1871001Notes

Reaction equation

HRID 1871001 reaction equation
[ClH:1].Cl.[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH:4]1[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[N:24]=[C:23](N(C)C)[CH:22]=[CH:21][N:20]=1.Cl.[H][H].C[OH:32]>[Pd].CC(O)C>[ClH:1].[ClH:1].[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH:4]1[CH2:13][NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[NH:24][C:23](=[O:32])[CH2:22][CH2:21][N:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86753238HCID 86753238, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18694187HCID 18694187, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of (±)-N2 -[3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]amino]propyl]N4,N4 -dimethyl-2,4-pyrimidinediamine dihydrochloride (0.0067 mol) in methanol (150 ml) was hydrogenated with palladium on activated carbon 10% (2 g) as a catalyst in the presence of a solution of hydrochloric acid in 2-propanol (2 ml). After uptake of hydrogen (2 eq.), the catalyst was filtered off. The filtrate was evaporated and the residue was crystallized twice from methanol. The crystals were filtered off and dried, yielding 0.32 g (13.1%) of (±)-2-[[3-[[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]amino]propyl]amino]-5,6-dihydro-4(3H)-pyrimidinone dihydrochloride; mp. 273.6° C. (comp. 12-c).

Workup

  1. customThe filtrate was evaporated
  2. customthe residue was crystallized twice from methanol
  3. filtrationThe crystals were filtered off
  4. customdried

Sources & evidence

ORD record
ord-3fca48757c2d43a3908b156071285298
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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