Bromine → N2-Mesityl-N7,N7-dipropyl[1,3]thiazolo[4,5-b]pyridine-2,7-diamine

HRID 2235490Notes

Reaction equation

HRID 2235490 reaction equation
[CH2:1]([N:4]([CH2:24][CH2:25][CH3:26])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])=[S:13])[CH:6]=1)[CH2:2][CH3:3].BrBr>C(O)(=O)C>[C:20]1([CH3:21])[CH:19]=[C:18]([CH3:22])[CH:17]=[C:16]([CH3:23])[C:15]=1[NH:14][C:12]1[S:13][C:6]2[C:7]([N:11]=1)=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:1][CH2:2][CH3:3])[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 860491941-[4-(Dipropylamino)pyridin-2-yl]-3-mesitylthiourea

Product 1

HCID 58896537N2-Mesityl-N7,N7-dipropyl[1,3]thiazolo[4,5-b]pyridine-2,7-diamineYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 0.040 g (0.11 mmol) of 1-[4-(Dipropylamino)pyridin-2-yl]-3-mesitylthiourea in 2 mL of glacial acetic acid was added 6.1 μL (0.12 mmol) of bromine. After 30 min at room temperature, an additional 2 μL of bromine was added. The reaction mixture was concentrated after 2 h and washed with ethyl acetate/hexanes. The organics were concentrated and the resulting oil was purified by flash chromatography eluting with a 4% methanol/dichloromethane mixture to give 0.020 g (50%) of the title compound as a light yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated after 2 h
  2. washwashed with ethyl acetate/hexanes
  3. concentrationThe organics were concentrated
  4. customthe resulting oil was purified by flash chromatography
  5. washeluting with a 4% methanol/dichloromethane mixture

Sources & evidence

ORD record
ord-8b5adb2efbdb4a96aefd7dc4cddee82d
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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