Ammonium Hydroxide → 5-bromo-7-[(methyloxy)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1910020Notes

Reaction equation

HRID 1910020 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][O:13][CH3:14])[CH:3]=1.[OH-].[NH4+:16]>>[Br:1][C:2]1[C:10]2[C:9]([NH2:16])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][O:13][CH3:14])[CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 866636815-bromo-4-chloro-7-[(methyloxy)methyl]-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 668236285-bromo-7-[(methyloxy)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 71%

Conditions

Temperature
100 °C

Procedure

5-bromo-4-chloro-7-[(methyloxy)methyl]-7H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.723 mmol) was transferred to a 5 mL microwave vial and then ammonium hydroxide (1.5 mL, 38.5 mmol) was added. The mixture was heated in microwave reactor at 100° C. for 30 minutes. The solid was isolated by filtration and dried to give 5-bromo-7-[(methyloxy)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (132 mg, 71.0% yield) as a white solid. LC-MS (ES) m/z=257.0, 259.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.14 (s, 1H), 7.56 (s, 1H), 6.81 (br. s., 2H), 5.43 (s, 2H), 3.21 (s, 3H).

Workup

  1. customThe solid was isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-c959ae7c78824f579da55e561dfd6e07
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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