Boron tribromide → HCID 19597475, compound

HRID 611525Notes

Reaction equation

HRID 611525 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[C:7]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=3)=[CH:13][N:12]([CH:23]([CH3:25])[CH3:24])[C:8]=2[N:9]=[CH:10][N:11]=1>ClCCl>[NH2:5][C:6]1[C:7]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)=[CH:13][N:12]([CH:23]([CH3:25])[CH3:24])[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 195974095-(4-Methoxyphenyl)-7-(1-methylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 19597475HCID 19597475, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of boron tribromide (14.4 ml of a 1M solution in dichloromethane) was added dropwise to a stirred solution of 4-amino-7-isopropyl-5-(4-methoxyphenyl) pyrrolo[2,3-d]pyrimidine (1.35 g) in dichloromethane (100 ml) at -10° C. under nitrogen. The reaction mixture was allowed to warm to 0° C. and stirred at this temperature for one hour. Additional boron tribromide (9.6 ml of a 1M solution in dichloromethane) was added at -10° C. and the mixture was allowed to warm to 0° C. and stirred for a further hour. The reaction mixture was quenched by the dropwise addition of saturated sodium bicarbonate solution (50 ml). The mixture was allowed to stand overnight and the dichloromethane layer separated off. Insoluble material at the interface was removed by filtration and dried to yield 4-amino-5-(4-hydroxyphenyl)-7-isopropylpyrrolo-[2,3-d]pyrimidine. The structure was confirmed by 1H nmr.

Workup

  1. temperatureto warm to 0° C.
  2. stirringstirred for a further hour
  3. customThe reaction mixture was quenched by the dropwise addition of saturated sodium bicarbonate solution (50 ml)
  4. waitto stand overnight
  5. customthe dichloromethane layer separated off
  6. customInsoluble material at the interface was removed by filtration
  7. customdried

Sources & evidence

ORD record
ord-c2472e42943e4e92a73cc8066a900c3a
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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