Diethyl Ether → HCID 178418613, compound

HRID 5963Notes

Reaction equation

HRID 5963 reaction equation
[CH3:1][C:2]([Si:5]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[O:6][CH:7]1[CH:10]([CH2:11][O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH:8]1[NH2:30])([CH3:4])[CH3:3].[NH2:43][C:44]1[N:49]=[C:48]([OH:50])[C:47]([N+:51]([O-:53])=[O:52])=[C:46](Cl)[N:45]=1.C(N(CC)CC)C.C(OCC)C>CN(C=O)C>[NH2:43][C:44]1[N:49]=[C:48]([OH:50])[C:47]([N+:51]([O-:53])=[O:52])=[C:46]([NH:30][CH:8]2[CH2:9][CH:10]([CH2:11][O:12][Si:13]([C:26]([CH3:27])([CH3:28])[CH3:29])([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:7]2[O:6][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:45]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 197942512-(((1,1-Dimethylethyl)diphenylsilyl)oxy)-3-(((1,1-dimethylethyl)-diphenylsilyl)oxymethyl)-1-aminocyclobutane2×HCID 178418667HCID 178418667, compound

Product 1

HCID 178418613HCID 178418613, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1- dimethylethyl)diphenyl-silyl)oxymethyl)-1-aminocyclobutane (588 mg, 0.99 mmol), the product of Step N, 189 mg (0.99 mmol) of 2-amino-6-chloro-4-hydroxy-5-nitropyrimidine (prepared as described by J. F. Constant, et al. in J. Heterocyclic Chem, 1035 (1985)) and triethylamine (220 μL, 1.50 mmol) were combined in 5 mL of anhydrous DMF. The reaction mixture was stirred in an oil bath at 50° C. under a nitrogen atmosphere for 2.5 h. Diethyl ether (200 mL) was added and the ether solution was washed with 2×50 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue (800 mg) was dissolved in methylene chloride and purified on a 1.0×45 cm silica gel column eluted @ 10 psi with 100 mL of methylene chloride, followed by 100 mL of 2% methanol in methylene chloride and finally 100 mL of 4% methanol in methylene chloride, to give 473 mg (64% yield) of the title compound; MS DCI-NH3M/Z: 748 (M+H)+ ; 1H NMR (CDCl3) δ 2.13-2.33 (m, 3H), 2.89 (s, 1H), 2.97 (s, 1H), 3.59-3.70 (m, 2H), 4.26 (t, 1H), 4.65 (m, 1H), 7.30-7.47 (m, 10H), 7.56-7.60 (m, 10H).

Workup

  1. washthe ether solution was washed with 2×50 mL of water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue (800 mg) was dissolved in methylene chloride
  6. custompurified on a 1.0×45 cm silica gel column
  7. washeluted @ 10 psi with 100 mL of methylene chloride

Sources & evidence

ORD record
ord-49aff4ea23944bc0a96ad4f0565e2869
Source dataset
uspto-grants-1993_09
Patent number
US05246931

Reaction notes

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