Phenethylamine → HCID 19014331, compound

HRID 1728552Notes

Reaction equation

HRID 1728552 reaction equation
[NH:1]([C:8]1[C:13]([CH2:14][C:15]([O:17]C)=O)=[C:12](Cl)[N:11]=[C:10]([CH3:20])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([CH2:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([CH2:28][NH:29][C:12]1[C:13]2[CH2:14][C:15](=[O:17])[N:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[N:9]=[C:10]([CH3:20])[N:11]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 86747976HCID 86747976, compound

Product 1

HCID 19014331HCID 19014331, compoundYield 44.6%

Conditions

Temperature
160 °C

Procedure

A mixture of 4-anilino-6-chloro-2-methylpyrimidine-5-acetic acid, methyl ester (5.0g, 17.2mM) and benzylmethylamine (2.22ml, 17.2mM) was heated at 160° C. for 3.5 hours. The mixture was cooled and then partitioned between methylene chloride (50ml) and 2M hydrochloric acid (50ml). The organic layer was separated, washed with a solution of sodium hydroxide (2M, 50ml), water, dried and the solvent evaporated. The residue was purified by flash column chromatography on silica (Merck 9385), eluting with ethyl acetate/hexane (20:80, v/v) to give 4-(N-benzylmethylamino)-2-methyl-6-oxo-7-phenyl-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidine (2.64g, 44.6%) m.p. 81°-84° C.; microanalysis, found; C, 73.0; H, 6.0; N, 16.3%; C21H20H40 requires C, 73.3; H, 5.8; N, 16.3%; NMR: DMSOd6 : 2.3(3H, s, pyrimidine-CH3), 3.2(3H,s,N-CH3), 3.95(2H,s,COCH2), 4.85(2H,s,N-CH2), 7.2-7.55(10H, complex, aromatic).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between methylene chloride (50ml) and 2M hydrochloric acid (50ml)
  3. customThe organic layer was separated
  4. washwashed with a solution of sodium hydroxide (2M, 50ml), water
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was purified by flash column chromatography on silica (Merck 9385)
  8. washeluting with ethyl acetate/hexane (20:80

Sources & evidence

ORD record
ord-914c25346ab64951a8a16fc36e8d38ab
Source dataset
uspto-grants-1994_07
Patent number
US05328910

Reaction notes

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