Water → HCID 21922581, compound

HRID 1244761Notes

Reaction equation

HRID 1244761 reaction equation
[N:1]1([C:7]2[N:15]=[C:14]3[C:10]([NH:11][CH:12]=[N:13]3)=[C:9]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29]Cl.O>CN(C=O)C.C(OCC)(=O)C>[N:1]1([C:7]2[N:15]=[C:14]3[C:10]([N:11]([CH2:29][O:28][CH2:27][CH2:26][Si:25]([CH3:32])([CH3:31])[CH3:24])[CH:12]=[N:13]3)=[C:9]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 52530822,6-Bis(morpholin-4-yl)-9H-purine

Product 1

HCID 21922581HCID 21922581, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

As shown in Scheme 5 above, 2,6-dicloropyrimidine (1 g, 5.29 mmol) was dissolved in morpholine (5 mL) in a sealed tube. The tube was heated to 120° C. for 5 hours then cooled to room temperature. Water (100 mL) was added and the resulting precipitate was filtered and washed with water to give 2,6-di-morpholin-4-yl-7H-purine (1.33 g, 87%). 2,6-Di-morpholin-4-yl-7H-purine (1.33 g, 4.58 mmol) was dissolved in DMF (50 mL). NaH (0.22 g, 5.50 mmol, 60% dispersion in oil) was added and the reaction was stirred at room temperature for 30 min. 2-(Trimethylsilyl)ethoxymethyl chloride (0.92 g, 5.50 mmol) was added dropwisely and the reaction was stirred for 18 h at room temperature. Water (200 mL) then ethyl aceate (200 mL) were added. The ethyl acetate extracts were washed with water (3×100 mL), dried over MgSO4, filtered and evaporated to dryness. The resulting residue was purified by silicagel column chromatography eluting with a gradient of 1:1 ethyl aceate to ethyl acetate to produce 2,6-Di-morpholin-4-yl-7-(2-trimethylsilanylethoxymethyl)-7H-purine (1.51 g, 78% yield).

Workup

  1. stirringthe reaction was stirred for 18 h at room temperature
  2. washThe ethyl acetate extracts were washed with water (3×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting residue was purified by silicagel column chromatography
  7. washeluting with a gradient of 1:1 ethyl aceate to ethyl acetate

Sources & evidence

ORD record
ord-6d8b2446094043dba3cce939bf9e7f5a
Source dataset
uspto-grants-2006_10
Patent number
US07122665B2

Reaction notes

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