Diisopropylethylamine → 3-{6-[(2,2-Dimethyl-propyl)-methyl-amino]-5-nitro-pyrimidin-4-ylamino}-4,N-dimethyl-benzamide

HRID 852053Notes

Reaction equation

HRID 852053 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:9])[C:3]=1[N+:15]([O-:17])=[O:16].[NH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([NH:24][CH3:25])=[O:23].CCN(C(C)C)C(C)C>O1CCOCC1>[CH3:12][C:11]([CH3:14])([CH3:13])[CH2:10][N:8]([CH3:9])[C:4]1[N:5]=[CH:6][N:7]=[C:2]([NH:18][C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:22]([NH:24][CH3:25])=[O:23])[C:3]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 126079733-Amino-N,4-dimethylbenzamideHCID 58928507(6-Chloro-5-nitro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-methyl-amine

Product 1

HCID 102001653-{6-[(2,2-Dimethyl-propyl)-methyl-amino]-5-nitro-pyrimidin-4-ylamino}-4,N-dimethyl-benzamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

(6-Chloro-5-nitro-pyrimidin-4-yl)-(2,2-dimethyl-propyl)-methyl-amine (1.0 mmol) was dissolved in p-dioxane (2 mL), and 3-amino-4,N-dimethyl-benzamide (0.2 g, 1.2 mmol) and DIEA (0.3 mL) were added. The resulting mixture was heated to 80° C. for overnight. The product (0.31 g, yield 80%) was purified by column silica gel chromatography. MS (m/z): 387 (M+H).

Sources & evidence

ORD record
ord-3d555c5c3b8640c3bf314c0647dff6ca
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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