2-Amino-4-methylpyridine → 2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-N-(4-methyl-pyridin-2-yl)acetamide

HRID 1663201

Reaction equation

HRID 1663201 reaction equation
[CH3:1][C:2]1[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]([CH2:8][C:9]([OH:11])=O)[CH:7]=1.[CH3:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH3:1][C:2]1[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]([CH2:8][C:9]([NH:21][C:17]2[CH:16]=[C:15]([CH3:14])[CH:20]=[CH:19][N:18]=2)=[O:11])[CH:7]=1

Participants

6

Reactant 4

HCID 15332-Amino-4-methylpyridineHCID 8471TriethylamineHCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 247451702-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-N-(4-methyl-pyridin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetic acid (75 mg, 0.4 mmol), 4-methylpyridin-2-amine (44 mg, 0.4 mmol), HBTU (151 mg, 0.4 mmol) and 0.1 mL of Et3N in DMF (5 mL) was stirred at room temperature for 2 hours to provide the title compound, which was then purified by HPLC. 1H NMR (400 MHz, DMSO-d6) δ: 11.37 (s, 1H), 10.97 (s, 1H), 8.20 (d, J=8.0 Hz, 1H), 7.81 (s, 1H), 7.51 (s, 1H), 7.03 (d, J=8.0 Hz, 1H), 4.58 (s, 2H), 2.33 (s, 3H), 1.77 (s, 3H). [M+H] calc'd for C13H14N4O2, 275; found, 275.

Sources & evidence

ORD record
ord-45ccae9971ee40cc8e3ac3e0296fb6a9
Source dataset
uspto-grants-2011_10
Patent number
US08034822B2

Linked notes

Loading…