Ammonium Hydroxide → HCID 86592315, compound

HRID 131202Notes

Reaction equation

HRID 131202 reaction equation
[CH:1]([C:4]1[N:5]=[C:6](O)[C:7]2[S:12][CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:3])[CH3:2].[NH4+].[OH-].O=P(Cl)(Cl)[Cl:18]>C(Cl)(Cl)Cl>[Cl:18][C:6]1[C:7]2[S:12][CH:11]=[CH:10][C:8]=2[N:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 178440209HCID 178440209, compound

Product 1

HCID 86592315HCID 86592315, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 2-isopropylthieno[3,2-d]pyrimidine-4-ol (1.66 g, 8.56 mmol) in POCl3 (30 mL) was refluxed for 1 h, cooled, diluted with chloroform (100 mL) and poured into a mixture of ice and NH4OH (150 mL). The organic phase was separated, washed with saturated NaHCO3 (20 mL), water and brine, dried (MgSO4) and concentrated in vacuo to give the title compound (2.01 g, 99%) as a pale yellow solid: IR νmax (Nujol)/cm−1 3065, 2960, 2926, 2855, 1561, 1513, 1457, 803; NMR δH (400 MHz, CDCl3) 1.40 (6H, d J 6.5 Hz), 3.38 (1H, heptet, J 6.5 Hz), 7.60 (1H, d J 5.0 Hz), 8.05 (1H, d, J 5.0 Hz).

Workup

  1. temperaturewas refluxed for 1 h
  2. temperaturecooled
  3. customThe organic phase was separated
  4. washwashed with saturated NaHCO3 (20 mL), water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30a9857da3fc468690da2aac8c51d315
Source dataset
uspto-grants-2008_06
Patent number
US07384949B2

Reaction notes

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