Methanol → 2-chloro-9-cyclopentyl-N-[2-[[(3,5-dichlorophenyl) methyl]-amino]-ethyl]-9H-purin-6-amine

HRID 1244942Notes

Reaction equation

HRID 1244942 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:13]=[C:12]([Cl:14])[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CO.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([Cl:31])[CH:30]=1)[CH:26]=O.[BH3-]C#N.[Na+]>C(O)(=O)C>[Cl:14][C:12]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:5]([NH:4][CH2:3][CH2:2][NH:1][CH2:26][C:25]2[CH:24]=[C:23]([Cl:22])[CH:30]=[C:29]([Cl:31])[CH:28]=2)[N:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 357463,5-DichlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Product 1

HCID 184575382-chloro-9-cyclopentyl-N-[2-[[(3,5-dichlorophenyl) methyl]-amino]-ethyl]-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

281 mg of the product obtained in Stage 1 of Example 7, 4 ml of methanol, 0.16 ml of 3,5-dichloro-benzaldehyde and 0.2 ml of acetic acid are mixed together, the reaction medium is agitated for 2 hours and 30 minutes, 0.1 g of NaBH3CN is added and agitation is carried out at ambient temperature for 1 hour. After evaporating the solvent, the residue is chromatographed on silica eluting with CH2Cl2/methanol/ammonium hydroxide (95/0.5/0.33) and 119 mg of expected product is obtained.

Workup

  1. waitagitation is carried out at ambient temperature for 1 hour
  2. customAfter evaporating the solvent
  3. customthe residue is chromatographed on silica eluting with CH2Cl2/methanol/ammonium hydroxide (95/0.5/0.33)

Sources & evidence

ORD record
ord-9bc2dbf9c37e4624b22989ee585dbe06
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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