Triethylamine → 4-(2-Indanylamino)-5,6-dimethylthieno[2,3-d]pyrimidine

HRID 48417Notes

Reaction equation

HRID 48417 reaction equation
O[C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.P(Cl)(Cl)(Cl)=O.[NH2:18][CH:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1.C(N(CC)CC)C>C(O)C>[CH2:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][CH:19]1[NH:18][C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 763102-AminoindaneHCID 178435036HCID 178435036, compound

Product 1

HCID 227196144-(2-Indanylamino)-5,6-dimethylthieno[2,3-d]pyrimidineYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using 4-hydroxy-5,6-dimethylthieno[2,3-d]pyrimidine (180 mg, 1.0 mmol), phosphorus oxychloride (1.0 ml), 2-aminoindan (270 mg, 2.0 mmol), triethylamine (0.84 ml, 6.0 mmol) and dry ethanol (5 ml), a similar procedure to b) in Production Example 208 was carried out. The product obtained was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (190 mg, 0.64 mmol) having the following physical properties:

Workup

  1. customThe product obtained
  2. customwas purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-51395a05444f46d9868bff3dc9b97a77
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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