Benzene, 1-isocyanato-2-methoxy- → HCID 178489603, compound

HRID 1500042Notes

Reaction equation

HRID 1500042 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]=[O:20]>CN(C=O)C>[F:8][C:7]1[C:2]([NH:1][C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH3:10])=[O:20])=[N:3][C:4]([OH:9])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 69695Benzene, 1-isocyanato-2-methoxy-HCID 178509007HCID 178509007, compound

Product 1

HCID 178489603HCID 178489603, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a magnetically stirred mixture of 4-amino-2-hydroxy-5-fluoropyrimidine (150 mg, 1.16 mmol) in dry DMF (3.5 mL) was added 2-methoxyphenyl isocyanate (170 μL, 1.28 mmol) and the white suspension was allowed to stir at room temperature for 60 min. The mixture was heated to 55° C. for 3 h, and then allowed to stir at room temperature overnight. The precipitate was collected by vacuum filtration and washed with Et2O (10×3 mL) to give a solid material, which was air dried for 1 h to give 1-(5-fluoro-2-hydroxypyrimidin-4-yl)-3-(2-methoxyphenyl)urea (269 mg, 83%) as a white solid: mp 247-250° C.; 1H NMR (300 MHz, DMSO-d6) δ 12.24 (bs, 1H), 11.31 (bs, 1H), 10.16 (bs, 1H), 8.14 (d, J=7.91 Hz, 1H) 8.0 (d, J=5.6, 1H), 7.03-6.99 (m, 2H), 6.95-6.88 (m, 1H), 3.87 (s, 3H) MS (ESI) m/z 276.9 (M−H)−.

Workup

  1. temperatureThe mixture was heated to 55° C. for 3 h
  2. stirringto stir at room temperature overnight
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with Et2O (10×3 mL)
  5. customto give a solid material, which
  6. customdried for 1 h

Sources & evidence

ORD record
ord-9d96f741523449a0bf6773e026cd30d0
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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