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

HRID 1910033Notes

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][N: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][N:14]([CH3:16])[CH3:15])[CH:3]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 86663684[2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]dimethylamine

Product 1

HCID 668236955-bromo-7-[2-(dimethylamino)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 116.1%

Conditions

Temperature: 100 °C

Procedure

To [2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]dimethylamine (175 mg, 0.576 mmol) was added ammonium hydroxide (22.45 μl, 0.576 mmol) in to a 5 ml sealable vial. The vial was then capped and heated at 100° C. overnight. The reaction was cooled to room temperature and concentrated to a light brown oil of 5-bromo-7-[2-(dimethylamino)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (190 mg, 0.669 mmol, 116% yield), which was used without further purification. LC/MS (ES) m/z=284.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ8.14 (s, 1H), 7.53 (s, 1H), 6.82 (br. s., 2H), 4.48 (t, J=6.32 Hz, 2H), 3.41 (br. s., 2H), 2.71 (s, 6H).

Workup

customThe vial was then capped
temperatureThe reaction was cooled to room temperature

Sources & evidence

ORD record: ord-6525d7c8c2fd48269c3f47da2b981410
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598156B2

Reaction notes

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