Diisopropylethylamine → HCID 86633860, compound

HRID 1687019Notes

Reaction equation

HRID 1687019 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[C:4](Cl)[N:3]=1.[NH2:11][C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([NH:16][CH3:17])=[O:15].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([NH:16][CH3:17])=[O:15])[C:5]([C:8]#[N:9])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3080722-Amino-N-methylbenzamideHCID 140269072,4-Dichloro-5-cyanopyrimidine

Product 1

HCID 86633860HCID 86633860, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a similar fashion as outlined in Example 191a, 2,6-dichloro-5-cyanopyrimidine was reacted with 2-amino-N-methylbenzamide and N,N-diisopropylethylamine in isopropyl alcohol (no microwave—20° C., 10 minutes) to afford 2-(2-chloro-5-cyano-pyrimidin-4-ylamino)-N-methyl-benzamide as a yellow solid. Mp: 228-32° C. (dec); MS: 288.26 (M+H); 1H NMR (chloroform-d): δ 12.49 (s, 1H), δ 8.69 (d, J=8 Hz, 1H), δ 8.50 (s, 1H), δ 7.57 (m, 2H), δ 7.22 (t, J=8 Hz, 1H), δ 6.31 (br s, 1H), δ 3.08 (d, J=5 Hz, 3H).

Sources & evidence

ORD record
ord-6bd21af14aa541a186b1a3098d7beb26
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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