Ammonium Hydroxide → 5-Bromo-7-isopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1910030Notes

Reaction equation

HRID 1910030 reaction equation
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:3]=1.[OH-].[NH4+:18]>>[Br:1][C:2]1[C:10]2[C:9]([NH2:18])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 866636835-bromo-4-chloro-7-(3-methylbutyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 668237945-Bromo-7-isopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 97.3%

Procedure

To 5-bromo-4-chloro-7-(3-methylbutyl)-7H-pyrrolo[2,3-d]pyrimidine (210 mg, 0.694 mmol) in a 5 mL sealable vial was added ammonium hydroxide (1.5 mL, 38.5 mmol). The mixture was then capped and heated at room temp overnight. The reaction was cooled and a precipitate formed. The solid was isolated by filtration and air dried to isolated 5-bromo-7-(3-methylbutyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (191 mg, 0.675 mmol, 97% yield) as a light brown solid. For 50-A1: LC/MS (ES) m/z=283.2, 285.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6) 8.10 (s, 1H), 7.48 (s, 1H), 6.70 (br. s., 2H), 4.12 (t, J=7.20 Hz, 2H), 1.64 (q, J=6.99 Hz, 2H), 1.44 (ddd, J=6.69, 6.82, 13.26 Hz, 1H), 0.90 (d, J=6.57 Hz, 6H).

Workup

  1. customThe mixture was then capped
  2. temperatureThe reaction was cooled
  3. customa precipitate formed
  4. customThe solid was isolated by filtration and air
  5. customdried

Sources & evidence

ORD record
ord-81294315eec94bdc84531cc5e830046e
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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