Triethylamine → (R,E)-ethyl 3-(2-amino-4-methyl-6-(tetrahydrofuran-3-ylamino)pyrimidin-5-yl)acrylate

HRID 422000Notes

Reaction equation

I[C:2]1[C:3]([NH:10][C@@H:11]2[CH2:15][CH2:14][O:13][CH2:12]2)=[N:4][C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH:17]=[CH2:18].C(N(CC)CC)C>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>[NH2:9][C:5]1[N:6]=[C:7]([CH3:8])[C:2](/[CH:18]=[CH:17]/[C:16]([O:20][CH2:21][CH3:22])=[O:19])=[C:3]([NH:10][C@@H:11]2[CH2:15][CH2:14][O:13][CH2:12]2)[N:4]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine (4.53 g, 14.2 mmol), ethyl acrylate (4.25 g, 42.5 mmol) and triethylamine (4.30 g, 42.5 mmol) in DMF (150 mL) was added Pd(PPh3)4 (1.635 g, 10 mol %) under nitrogen at room temperature. The resulting mixture was heated to 95° C. for 18 h under a nitrogen atmosphere. After the reaction was complete by LC/MS, the resulting mixture was concentrated under reduced pressure and directly subjected to column chromatography purification to give (R,E)-ethyl 3-(2-amino-4-methyl-6-(tetrahydrofuran-3-ylamino)pyrimidin-5-yl)acrylate (3.90 g, 94% yield). MS (EI) for C14H20N4O: 293.2 (MH+).

Workup

concentrationthe resulting mixture was concentrated under reduced pressure
customdirectly subjected to column chromatography purification

Sources & evidence

ORD record: ord-16cd7e9ffaab4e2484a8b4063f95b655
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101622B2

Reaction notes

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