2-Methyl-3-butyn-2-ol → HCID 21955995, compound

HRID 2212875Notes

Reaction equation

HRID 2212875 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=3)[N:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:27][C:28]([OH:32])([C:30]#[CH:31])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.C(NC(C)C)(C)C.[Cu](I)I>[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:31]#[C:30][C:28]([OH:32])([CH3:29])[CH3:27])[CH:21]=3)[N:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

7

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 11776TriphenylphosphineHCID 21955984HCID 21955984, compound

Product 1

HCID 21955995HCID 21955995, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 7912DiisopropylamineSolvent

Procedure

A suspension of N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-iodo-phenyl)-amine (300 mg, 0.64 mmol) and 2-methyl-3-butyn-2-ol (110 mg, 1.3 mmol) in dimethylformamide (20 ml) and diisopropylamine (5 ml) are stirred in the presence of bis triphenylphosphine palladiumdichloride (20 mg), triphenylphosphine (20 mg) and copper iodide under a nitrogen atmosphere for 16 hours. After an aqueous work-up the residue is purified by chromatography (eluent: 1:2 mixture of ethyl acetate/hexane) to give the N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-[3-(3-hydroxy-3-methyl-1-butynyl)-phenyl]-amine, m.p. 262–263° C.

Workup

  1. customAfter an aqueous work-up the residue is purified by chromatography (eluent: 1:2 mixture of ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d487ac9b43b1405aa69cf79a7f027f5c
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

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