2,4,5-Trichloropyrimidine → 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-N-prop-2-ynyl-benzamide

HRID 1687749Notes

Reaction equation

HRID 1687749 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([N:6]([CH3:10])[CH2:7][C:8]#[CH:9])=[O:5].[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([Cl:23])=[CH:18][N:17]=1>>[Cl:15][C:16]1[N:21]=[C:20]([NH:1][C:2]2[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=2[C:4]([N:6]([CH3:10])[CH2:7][C:8]#[CH:9])=[O:5])[C:19]([Cl:23])=[CH:18][N:17]=1

Participants

3

Reactant 2

HCID 2372592,4,5-TrichloropyrimidineHCID 158702202-amino-N-methyl-N-prop-2-ynyl-benzamide

Product 1

HCID 866340272-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-N-prop-2-ynyl-benzamide

Procedure

2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-N-prop-2-ynyl-benzamide was prepared from 2-amino-N-methyl-N-prop-2-ynyl-benzamide and 2,4,5-trichloro-pyrimidine in an analogous manner to Example 1387b. Product isolated as a yellow foam (958 mg, 12%). LCMS (m/e) 335 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 9.45 (s, 1H), 8.35 (d, 1H, J=8.3 Hz), 8.22 (s, 1H), 7.63-7.30 (m, 2H), 7.25-7.17 (m, 1H), 4.53-4.01 (m, 2H), 3.19 (s, 3H), 2.46-2.24 (m, 1H).

Sources & evidence

ORD record
ord-15bb1735ea514316ac19e326dd98d28a
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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