Methanol → HCID 21923005, compound

HRID 1244906Notes

Reaction equation

HRID 1244906 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.[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1)#[N:21].CO.[BH3-]C#N.[Na+]>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][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([C:20]#[N:21])=[CH:23][CH:24]=2)[N:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Product 1

HCID 21923005HCID 21923005, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

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, 184 mg of 4-cyano-benzaldehyde in place of the benzaldehyde, 4 ml of methanol and 0.2 ml of acetic acid and 0.5 ml of tetrahydrofuran then the reaction medium is agitated at ambient temperature for approximately 5 hours. then 100 mg of NaBH3CN is added and agitation is carried out at ambient temperature for 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/hydroxylamine in a proportion of 95/05/0.33, 347 mg of expected product is obtained in the form of white crystals.

Workup

  1. waitagitation is carried out at ambient temperature for 1 hour
  2. addition10 ml AcOET is added
  3. washby washing with 2×5 ml H2O
  4. dry with material5 ml of a saturated aqueous solution of NaCl, drying
  5. customevaporating the solvent
  6. customAfter purification by chromatography on silica eluting with methylene chloride/methanol/hydroxylamine in a proportion of 95/05/0.33

Sources & evidence

ORD record
ord-d03cabbe36e74d87990fea23019f02cd
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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