Urea → HCID 22473437, compound

HRID 2183557Notes

Reaction equation

HRID 2183557 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([NH2:16])(=O)[CH2:11][C:12]([CH3:14])=O.[NH2:17][C:18]([NH2:20])=[O:19].C1COCC1>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[NH:20][C:18](=[O:19])[NH:17][C:12]([CH3:14])=[C:11]2[C:10]#[N:16])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 1176UreaHCID 8028TetrahydrofuranHCID 765833-BromobenzaldehydeHCID 80077Acetoacetamide

Product 1

HCID 22473437HCID 22473437, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-bromobenzaldehyde (13.0 g, 70 mmol), acetoacetamide (7.08 g, 70 mmol), urea (5.26 g, 87.5 mmol), polyphosphate ester (9.1 g, 21 mmol) and THF (150 mL) was heated in a sealed tube for 18 h at 75° C. This mixture was cooled to room temperature; more polyphosphate ester (60.6 g, 140 mmol) was added and heating resumed for another 5 h. The reaction mixture was cooled to room temperature, poured into water (800 mL) and stirred for 18 h. The resulting precipitates were collected by vacuum filtration, washed with water and with ether, and air dried to yield 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine as a light yellow solid (16.25 g; 79%): 1H NMR (DMSO-d6, 400 MHz) δ 9.60 (s, 1H), 7.87 (s, 1H), 7.55 (m, 1H), 7.48 (m, 1H), 7.39 (t, 1H, J=7.9 Hz), 7.32 (d, 1H, J=7.9 Hz), 5.14 (s, 1H), 2.02 (s, 3H).

Workup

  1. temperatureThis mixture was cooled to room temperature
  2. temperatureheating
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe resulting precipitates
  5. filtrationwere collected by vacuum filtration
  6. washwashed with water and with ether, and air
  7. customdried

Sources & evidence

ORD record
ord-55e5ca7c374b44cfb9ef168737f8771a
Source dataset
uspto-grants-2005_05
Patent number
US06900214B2

Reaction notes

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