4-Nitrophenylboronic acid → 4-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

HRID 611519Notes

Reaction equation

HRID 611519 reaction equation
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[N+:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([O-:17])=[O:16]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[C:3]2[C:10]([C:21]3[CH:22]=[CH:23][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=3)=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 27735524-Nitrophenylboronic acidHCID 195974264-Chloro-5-iodo-7-(propan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 195974814-Chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Procedure

In a similar manner to Example 10 b), 4-chloro-5-iodo-7-isopropylpyrrolo-[2,3-d]pyrimidine (0.57 g), was reacted with 4-nitrophenylboronic acid (0.30 g) using bis(triphenylphosphine)palladium (II) chloride (0.126 g) to give 4-chloro-7-isopropyl-5-(4-nitrophenyl)pyrrolo[2,3-d]pyrimidine which was reduced using a mixture of ammonium chloride (22 mg),iron powder (0.45 g) in water (2 ml) and industrial methylated spirit (10 ml) to give 4-chloro-5-(4-aminophenyl)-7-isopropylpyrrolo[2,3-d]pyrimidine which was reacted with ammonia in 1,4-dioxen in a sealed vessel to give 4-amino-5-(4-aminophenyl)-7-isopropyl-pyrrolo[2,3-d]pyrimidine.

Sources & evidence

ORD record
ord-b1c627cc878645ec8c80a05f99d363a3
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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