Potassium Carbonate → HCID 19955480, compound

HRID 1779413Notes

Reaction equation

HRID 1779413 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([OH:9])=[C:4]([CH3:10])[N:3]=1.Br[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:25])([F:24])[F:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:23])([F:24])[F:25])=[C:4]([CH3:10])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12289250HCID 12289250, compoundHCID 19955518HCID 19955518, compound

Product 1

HCID 19955480HCID 19955480, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to that of Step D of Example 12, using 2.4 grams (0.010 mole) of 2,4-diamino-5-hydroxy-6-methylpyrimidine hydrosulfate salt (prepared in Steps A-C of this Example), 3.0 grams (0.011 mole) of 2-trifluoromethylphenyl 3-bromopropyl ether, and 8.3 grams (0.060 mole) of finely ground potassium carbonate in 50 mL of N,N-dimethylformamide. The product was recrystallized from methanol and water, yielding 0.8 gram of 2,4-diamino-5-[3-(2-trifluoromethylphenoxy)propoxy]-6-methylpyrimidine, mp 132°-134° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 12
  2. customThe product was recrystallized from methanol and water

Sources & evidence

ORD record
ord-408e3814453347c4bc55b2b463f3e69d
Source dataset
uspto-grants-1997_05
Patent number
US05627189

Reaction notes

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