Methanol → HCID 21923004, compound

HRID 1244907Notes

Reaction equation

HRID 1244907 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.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[CH:25]=O.CO.[BH3-]C#N.[Na+]>CCOC(C)=O.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][CH2:25][C:24]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:22]([O:21][CH3:20])[CH:23]=2)[N:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 68583,4,5-TrimethoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Product 1

HCID 21923004HCID 21923004, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The operation is carried out as in Stage 2 of Example 7 starting from 280 mg of the product obtained in Stage 1 of Example 7, 275 mg of 3,4,5 trimethoxybenzaldehyde in place of the benzaldehyde, 4 ml of methanol and 0.2 ml of acetic acid then the reaction medium is agitated at ambient temperature for 5 hours. Then 100 mg of NaBH3CN is added and the reaction medium is agitated at ambient temperature for approximately 1 hour. 10 ml AcOEt is added, followed by washing with 2×5 ml H2O, then 5 ml of a saturated aqueous solution of NaCl, drying and evaporating the solvent. After purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 95/05/0.33, 305 mg of expected product is obtained in the form of white crystals.

Workup

  1. stirringthe reaction medium is agitated at ambient temperature for approximately 1 hour
  2. washby washing with 2×5 ml H2O
  3. dry with material5 ml of a saturated aqueous solution of NaCl, drying
  4. customevaporating the solvent
  5. customAfter purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 95/05/0.33

Sources & evidence

ORD record
ord-830c250547054bbb8521241207f47f6e
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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