Methanol → HCID 21922995, compound

HRID 1244901Notes

Reaction equation

HRID 1244901 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.[CH3:22][O:23][C:24]1[C:29]2[O:30][CH2:31][O:32][C:28]=2[CH:27]=[C:26]([CH:33]=O)[CH:25]=1.[BH3-]C#N.[Na+]>CCOC(C)=O.O1CCCC1.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][CH2:33][C:26]2[CH:25]=[C:24]([O:23][CH3:22])[C:29]3[O:30][CH2:31][O:32][C:28]=3[CH:27]=2)[N:13]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 220161,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-HCID 5003444Sodium cyanoborohydrideHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Product 1

HCID 21922995HCID 21922995, compoundYield 70.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 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, 4 ml of methanol, 250 mg of 7-methoxy-1,3-benzodioxole-5-carboxaldehyde in place of the benzaldehyde, 0.2 ml of acetic acid and 0.4 ml of tetrahydrofuran and the reaction medium is left for 4 hours at ambient temperature. Then 100 mg of NaBH3CN is added and agitation is carried out at ambient temperature for approximately 3 hours. 10 ml AcOEt is added, followed by washing with 2×5 ml H2O, then 5 ml of saturated aqueous solution of NaCl, followed by drying and evaporating the solvent and purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 90/10/1. In this way 311 mg of expected product is obtained in the form of beige crystals.

Workup

  1. waitagitation is carried out at ambient temperature for approximately 3 hours
  2. washby washing with 2×5 ml H2O
  3. customby drying
  4. customevaporating
  5. customthe solvent and purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 90/10/1

Sources & evidence

ORD record
ord-d552d30520864e5cb704ffef6cf8ab94
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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