4-chloro-5H-pyrrolo[3,2-d]pyrimidine → HCID 67520370, compound

HRID 1925939Notes

Reaction equation

HRID 1925939 reaction equation
[Cl:1][C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[NH2:15]>CN1CCCC1=O.C(OCC)(=O)C>[ClH:1].[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[C:3]3[NH:10][CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1

Participants

5

Reactant 2

HCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidineHCID 70592633-Chloro-4-(3-fluorobenzyloxy)aniline

Product 1

HCID 67520370HCID 67520370, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

4-Chloro-5H-pyrrolo[3,2-d]pyrimidine (770 mg) and 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (2.52 g) were dissolved in 1-methyl-2-pyrrolidone (10 mL), and the mixture was stirred with heating at 140° C. for 2.5 hrs. After cooling to room temperature, the mixture was diluted with ethyl acetate (300 mL), and stirred at room temperature for 1 hr. The precipitated powder was collected by filtration, washed with ethyl acetate (30 mL), and dried under reduced pressure to give the title compound (1.62 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringstirred at room temperature for 1 hr
  3. filtrationThe precipitated powder was collected by filtration
  4. washwashed with ethyl acetate (30 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a515fa950a49463ba310b42135fb09ba
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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