4-((5-Iodo-4-(methylamino)pyrimidin-2-yl)amino)benzonitrile → (S)-tert-butyl (1-((5-(2-((4-cyanophenyl)amino)-4-(methylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

HRID 2284768Notes

Reaction equation

HRID 2284768 reaction equation
I[C:2]1[C:3]([NH:17][CH3:18])=[N:4][C:5]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:19][N:20]([C@@H:28]([CH3:37])[C:29](=[O:36])[NH:30][CH2:31][CH2:32][CH2:33][C:34]#[CH:35])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>>[C:13]([C:12]1[CH:15]=[CH:16][C:9]([NH:8][C:5]2[N:4]=[C:3]([NH:17][CH3:18])[C:2]([C:35]#[C:34][CH2:33][CH2:32][CH2:31][NH:30][C:29](=[O:36])[C@@H:28]([N:20]([CH3:19])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[CH3:37])=[CH:7][N:6]=2)=[CH:10][CH:11]=1)#[N:14]

Participants

3

Reactant 2

HCID 900517884-((5-Iodo-4-(methylamino)pyrimidin-2-yl)amino)benzonitrileHCID 90052832(S)-tert-butyl methyl(1-oxo-1-(4-pentyn-1-ylamino)propan-2-yl)carbamate

Product 1

HCID 117861293(S)-tert-butyl (1-((5-(2-((4-cyanophenyl)amino)-4-(methylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

Procedure

By using 4-((5-iodo-4-(methylamino)pyrimidin-2-yl)amino)benzonitrile (F224) and (S)-tert-butyl methyl(1-oxo-1-(4-pentyn-1-ylamino)propan-2-yl)carbamate (U4), (S)-tert-butyl (1-((5-(2-((4-cyanophenyl)amino)-4-(methylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (J17) was obtained in the same manner as that of Example 38, (2).

Sources & evidence

ORD record
ord-d276337cc26f42cbb4f91b4b959e44f3
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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