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

HRID 1910026Notes

Reaction equation

HRID 1910026 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]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:3]=1.[OH-].[NH4+:21]>>[Br:1][C:2]1[C:10]2[C:9]([NH2:21])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 866636825-bromo-4-chloro-7-[2-(4-morpholinyl)ethyl]-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 668240265-bromo-7-[2-(4-morpholinyl)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 68%

Conditions

Temperature
100 °C

Procedure

To 5-bromo-4-chloro-7-[2-(4-morpholinyl)ethyl]-7H-pyrrolo[2,3-d]pyrimidine (240 mg, 0.694 mmol) in a 5 mL sealable vial was added ammonium hydroxide (1.5 mL, 38.5 mmol). The reaction vial was capped and heated at 100° C. overnight. The reaction was cooled and solid formed. The solid was isolated by filtration and the solid was washed with NH4OH. The solid was air dried to isolated the desired product 5-bromo-7-[2-(4-morpholinyl)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (154 mg, 68.0% yield) as an off white solid. LC-MS (ES) m/z=326.1 [M+H]+ 1H NMR (400 MHz, DMSO-d6) 8.10 (s, 1H), 7.47 (s, 1H), 6.69 (br. s., 2H), 4.22 (t, J=6.44 Hz, 2H), 3.52 (t, J=4.42 Hz, 4H), 2.65 (t, J=6.44 Hz, 2H), 2.41 (d, J=4.04 Hz, 4H).

Workup

  1. customThe reaction vial was capped
  2. temperatureThe reaction was cooled
  3. customsolid formed
  4. customThe solid was isolated by filtration
  5. washthe solid was washed with NH4OH
  6. customdried

Sources & evidence

ORD record
ord-81ef407f2fe141fba929b77d35a1668b
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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