Ammonia → Phenol, 4-[[2-amino-5-[(4-chlorophenyl)ethynyl]-4-pyrimidinyl]amino]-

HRID 1271034Notes

Reaction equation

HRID 1271034 reaction equation
N.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[C:12]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)=[N:13][C:14]([N:17]=CN(C(C)C)C(C)C)=[N:15][CH:16]=2)=[CH:5][CH:4]=1.NC1N=C(N)C(C#CC2C=CC(Cl)=CC=2)=CN=1>>[NH2:17][C:14]1[N:13]=[C:12]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=2)[C:11]([C:10]#[C:9][C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 184525515-[2-(4-Chlorophenyl)ethynyl]-2,4-pyrimidinediamineHCID 68567375HCID 68567375, compound

Product 1

HCID 9859020Phenol, 4-[[2-amino-5-[(4-chlorophenyl)ethynyl]-4-pyrimidinyl]amino]-

Procedure

The brown solution was evaporated in vacuo (bath temperature 30° C.) to obtain a brownish-burgundy solid. The residue was stirred in dichloromethane and filtered to yield 0.4 g of 5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneamino-4-(4-hydroxyanilino)pyrimidine. The 1H NMR spectrum (CDCL3) was consistent with this structure. A mixture of 0.37 g of this product was heated in a bomb with 32 mL of methanolic ammonia at a temperature of 100° C. for five hours. The cooled bomb contents were evaporated in vacuo and triturated with ice cold water and dried to yield a mixture of the desired 2-amino-5-(4-chlorophenylethynyl)-4-(4-hydroxyanilino)pyrimidine with 2,4-diamino-5-(4-chlorophenylethynyl)pyrimidine.

Workup

  1. customThe cooled bomb contents were evaporated in vacuo
  2. customtriturated with ice cold water
  3. customdried
  4. customto yield

Sources & evidence

ORD record
ord-5913615659234b8698310eaef4cf4a70
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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