Water → (5-Bromo(3-pyridyl))-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamine

HRID 1529816Notes

Reaction equation

HRID 1529816 reaction equation
Cl[C:2]1[C:7]2[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[Se:10][C:6]=2[N:5]=[CH:4][N:3]=1.[NH2:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Br:22])[CH:21]=1.[OH-].[Na+].O>CN(C=O)C>[Br:22][C:20]1[CH:21]=[C:16]([NH:15][C:2]2[C:7]3[C:8]4[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=4[Se:10][C:6]=3[N:5]=[CH:4][N:3]=2)[CH:17]=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 8176813-Amino-5-bromopyridineHCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 57377306(5-Bromo(3-pyridyl))-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamineYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene (500 mg, 1.84 mmol, from step b of example 1) in DMF (10 mL) was added sequentially 3-amino-5-bromopyridine (380 mg, 2.19 mmol) and powdered NaOH (220 mg, 5.5 mmol) at rt and the mixture was stirred at rt for 36 h. The mixture was poured into ice cooled water and stirred for 10 min. The precipitated solid was filtered, washed with water and dried. The crude solid was chromatographed over silica gel column using hexane-EtOAc (70:30) as eluents to give the product as an off-white color solid (500 mg, 67%), which was recrystallized from acetonitrile, mp 170-172° C. 1H NMR (400 MHz, CDCl3): δ 8.66 (1H, t, J=2.0 Hz), 8.56 (1H, d, J=2.4 Hz), 8.49 (1H, s), 8.39 (1H, d, J=1.6 Hz), 7.24 (1H, s, exchangeable with D2O), 3.08 (2H, t, J=6.2 Hz), 2.96 (2H, t, J=6.0 Hz), 2.00-2.06 (2H, m), 1.92-1.98 (2H, m); 13C NMR (100 MHz, CDCl3): δ 171.7, 154.7, 151.6, 145.3, 140.8, 140.0, 136.4, 130.3, 126.4, 120.5, 120.0, 28.4, 28.1, 22.7, 22.3; LC-MS (positive ion mode): m/z 407, 409, 411 (M+H)+.

Workup

  1. additionThe mixture was poured into ice
  2. stirringstirred for 10 min
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude solid was chromatographed over silica gel column

Sources & evidence

ORD record
ord-e12d9d84a34c4026b78b4701ceb9a8af
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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