Benzoyl chloride → Benzoic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl Ester

HRID 705579Notes

Reaction equation

HRID 705579 reaction equation
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:12][N:11]([CH:10]=[N:9][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]([O:8][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1)[CH3:13]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178484257HCID 178484257, compound

Product 1

HCID 57818967Benzoic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl EsterYield 94.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformamidine (0.10 g, 0.54 mmol) in pyridine (2 mL) was added benzoyl chloride (0.084 g, 0.60 mmol), and the mixture was agitated on an orbital shaker for 16 h at RT. The reaction mixture was partitioned between EtOAc and saturated aq NaHCO3, and the organic phase was dried over solid MgSO4, filtered, and evaporated to give the title compound (0.147 g 94%) as a white solid: mp 136-138° C.; 1H NMR (300 MHz, CDCl3) δ 8.69 (s, 1H), 8.27 (d, J=2.4 Hz, 2H), 8.25-8.20 (m, 2H), 7.69-7.63 (m, 1H), 7.56-7.49 (m, 2H), 3.23 (s, 3H), 3.20 (s, 3H); HPLC-MS (ESI) m/z 289 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and saturated aq NaHCO3
  2. dry with materialthe organic phase was dried over solid MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-bb488616f0434be7846fc97f08924851
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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