Guanidine Hydrochloride → HCID 57732438, compound

HRID 1365067Notes

Reaction equation

HRID 1365067 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([CH:14]([OH:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)=O.Cl.[NH2:24][C:25]([NH2:27])=[NH:26].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:26][C:25]1[N:27]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([CH:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[OH:21])[CH:8]=2)[CH:4]=[CH:3][N:24]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 57732419HCID 57732419, compound

Product 1

HCID 57732438HCID 57732438, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A 5 mL microwave tube was charged with (2E)-3-(dimethylamino)-1-{4-fluoro-3-[hydroxy(phenyl)methyl]phenyl}-2-propen-1-one (0.2 mmol), guanidine hydrochloride (0.4 mmol), potassium carbonate (0.6 mmol) and ethanol (3.5 mL). The reaction was heated to 150° C. for 600 s using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water and extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered and concentrated to dryness. Reconcentration from diethyl ether provided [5-(2-amino-4-pyrimidinyl)-2-fluorophenyl]-(phenyl)methanol as a white foam. H1 NMR (d6-dmso): 8.34 (dd, 1H), 8.26 (d, 1H), 7.93 (m, 1H), 7.31 (m, 4H), 7.21 (m, 2H), 7.05 (d, 1H), 6.67 (br s, 2H), 6.10 (d, 1H), 5.94 (d, 1H). Mass (ES+)=296.1 (100%).

Workup

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-324b05634be94cb9a2a58e50e91bc03a
Source dataset
uspto-grants-2011_02
Patent number
US07888503B2

Reaction notes

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