Triethylamine → HCID 57606977, compound

HRID 886803Notes

Reaction equation

HRID 886803 reaction equation
C(N(CC)CC)C.[CH2:8]([NH:15][C:16]1[C:21](I)=[C:20]([CH3:23])[N:19]=[C:18]([NH2:24])[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:25]([O:29][CH2:30][CH3:31])(=[O:28])[CH:26]=[CH2:27]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:30]([O:29][C:25](=[O:28])/[CH:26]=[CH:27]/[C:21]1[C:16]([NH:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:17][C:18]([NH2:24])=[N:19][C:20]=1[CH3:23])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 57606984HCID 57606984, compound

Product 1

HCID 57606977HCID 57606977, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

Triethylamine (7.60 mL, 54.5 mmol) was added to a suspension of N4-benzyl-5-iodo-6-methylpyrimidine-2,4-diamine (3.14 g, 10.9 mmol), ethyl acrylate (3.55 mL, 32.7 mmol) and Pd(PPh3)4 (629 mg, 0.545 mmol) in anhydrous DMF (20 mL). The reaction was heated to 95° C. under nitrogen. After 24 h, the reaction was allowed to cool to room temperature and concentrated in vacuo. The residue was poured into a 10% solution of LiCl and washed with ethyl acetate (100 mL). The organic phase was separated and washed with brine, separated and dried over Na2SO4. The filtrate was concentrated in vacuo and purified on SiO2 (3:2 methylene chloride:ethyl acetate) to afford (E)-ethyl-3-(2-amino-4-(benzylamino)-6-methylpyrimidin-5-yl)acrylate (0.954 g, 28% yield) as a light yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was poured into a 10% solution of LiCl
  4. washwashed with ethyl acetate (100 mL)
  5. customThe organic phase was separated
  6. washwashed with brine
  7. customseparated
  8. dry with materialdried over Na2SO4
  9. concentrationThe filtrate was concentrated in vacuo
  10. custompurified on SiO2 (3:2 methylene chloride:ethyl acetate)

Sources & evidence

ORD record
ord-de48cc4334324e479505cc43f36f7ed4
Source dataset
uspto-grants-2012_08
Patent number
US08247408B2

Reaction notes

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