Diisopropylethylamine → 2-(5-Bromo-2-chloro-pyrimidin-4-ylamino)-N-methyl-benzamide

HRID 1687017Notes

Reaction equation

HRID 1687017 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([Br:8])=[C:4](Cl)[N:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][CH3:16])=[O:14].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([NH:15][CH3:16])=[O:14])[C:5]([Br:8])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 3080722-Amino-N-methylbenzamide

Product 1

HCID 587484682-(5-Bromo-2-chloro-pyrimidin-4-ylamino)-N-methyl-benzamideYield 76%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a similar fashion as outlined in Example 191a, 2,6-dichloro-5-bromopyrimidine was reacted with 2-amino-N-methylbenzamide and N,N-diisopropylethylamine in isopropyl alcohol (microwave—120° C., 10 minutes) to afford 2-(2-chloro-5-bromo-pyrimidin-4-ylamino)-N-methyl-benzamide as a yellow solid in 76% yield. MS: 342.96 (M+H); 1H NMR (d6-dmso): δ 11.96 (s, 1H), δ 8.85 (br s, 1H), δ 8.57 (s, 1H), δ 8.47 (d, J=9 Hz, 1H), δ 7.79 (d, J=8 Hz, 1H), δ 7.57 (t, J=8 Hz, 1H), δ 7.22 (t, J=8 Hz, 1H), δ 2.78 (d, J=5 Hz, 3H).

Sources & evidence

ORD record
ord-47b67190797c4d83910fb38b56281dad
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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