Hydrochloric Acid → HCID 67695581, compound

HRID 1728553Notes

Reaction equation

HRID 1728553 reaction equation
[CH2:1]([CH2:8][NH:9][C:10]1[C:11]2[CH2:19][C:18](=O)[N:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]=2[N:13]=[C:14]([CH3:16])[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>O1CCCC1>[CH2:1]([CH2:8][NH:9][C:10]1[C:11]2[CH2:19][CH2:18][N:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]=2[N:13]=[C:14]([CH3:16])[N:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19014331HCID 19014331, compound

Product 1

HCID 67695581HCID 67695581, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1M BH3.THF complex in tetrahydrofuran (10.4ml, 9.2mM) was added dropwise, under an atmosphere of argon, to a stirred mixture of 4-(benzylmethylamino)-2-methyl-6-oxo-7-phenyl-5, 6-dihydro-7H-pyrrolo-[2,3-d]-pyrimidine (1.6g, 4.6mM) in dry tetrahydrofuran (105ml). The mixture was stirred at ambient temperature for 24 hours. The mixture was then added to 2M hydrochloric acid (100ml), the pH was adjusted to about pH7 using concentrated sodium hydroxide and then extracted with ethyl acetate (2×200ml). The organic layers were combined, dried and the solvent evaporated. The residue was purified by flash column chromotography on silica (Merck 9385), using a mixture of methylene chloride: hexane: ethyl acetate (10:8:1) as eluant to give 4[N-benzylmethylamino)-2-methyl-7-phenyl-5,6-dihydro-7H-pyrrolo-[2,3-d]-pyrimidine in the form of a pure solid with m.p. 105°-106° C.; microanalysis, found; C, 75.5; H, 6.7; N, 16.8%; C21H22N4.0.2H2 requires C, 75.6; H, 6.9; N, 16.8%. NMR: 2.47(3H,s,pyrimidine-CH3), 3.14(3H,s,N--CH3), 3.21(2H,t,N--CH2 --CH2 --), 3.91(2H,t,N--CH2--CH2--), 4.18(2H,s,N--CH2Ph), 6.99(1H,t,aromatic), 7.23-7.47(7H, complex, aromatic), 7.73(2H,d,aromatic); and a crude solid. The material was combined and used without further purification in the subsequent stage of the synthesis.

Workup

  1. extractionextracted with ethyl acetate (2×200ml)
  2. customdried
  3. customthe solvent evaporated
  4. customThe residue was purified by flash column chromotography on silica (Merck 9385)
  5. additiona mixture of methylene chloride: hexane: ethyl acetate (10:8:1) as eluant

Sources & evidence

ORD record
ord-a4d0e9de2aee4b9aab5b2b93f8775596
Source dataset
uspto-grants-1994_07
Patent number
US05328910

Reaction notes

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