Hydrochloric Acid → HCID 24903991, compound

HRID 1678021Notes

Reaction equation

HRID 1678021 reaction equation
[ClH:1].[CH3:2]N(C)C=O.C([O-])([O-])OCC.[CH2:13]([NH:20][C:21]1[C:26]([NH2:27])=[C:25](Cl)[N:24]=[CH:23][N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>O1CCOCC1>[Cl:1][C:23]1[N:22]=[C:21]2[C:26]([N:27]=[CH:2][N:20]2[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:25][N:24]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 258596n4-benzyl-6-chloropyrimidine-4,5-diamineHCID 53630039Ethylorthoformate

Product 1

HCID 24903991HCID 24903991, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4.0 M of hydrochloric acid in 1,4-dioxane (2.3 mL) in N,N-dimethylformamide (10.0 mL, 0.129 mol) was added ethyl orthoformate (2.00 mL, 0.0120 mol) and N4-benzyl-6-chloropyrimidine-4,5-diamine (500 mg, 0.002 mol). The mixture was stirred for 3 days. The reaction was quenched by addition of triethylamine (1.5 mL, 0.011 mol), extracted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, water, brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (3 to 5% MeOH/DCM) to obtain 336 g (60%). LC/MS: Rt=1.49 min, ES+ 245.08 (AA standard).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated aqueous sodium bicarbonate, water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (3 to 5% MeOH/DCM)
  7. customto obtain 336 g (60%)

Sources & evidence

ORD record
ord-21b5699915be4edf867e7120e0e1508d
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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