N,N-Dimethylaniline → HCID 86617827, compound

HRID 1660931Notes

Reaction equation

HRID 1660931 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[C:5](O)[C:6]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:7]=2[N:8]=1.O=P(Cl)(Cl)[Cl:19].CN(C)C1C=CC=CC=1>[NH4+].[OH-]>[Cl:19][C:5]1[C:6]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:7]=2[N:8]=[C:3]([NH2:2])[N:4]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178479161HCID 178479161, compound

Product 1

HCID 86617827HCID 86617827, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 2-amino-benzo[4,5]thieno[3,2-d]pyrimidin-4-ol hydrochloride (179 mg, 0.7 mmol), POCl3 (1.5 mL), and N,N-dimethylaniline (0.15 mL) was heated at 110° C. for 3 h. The mixture was cooled to rt and the resulting suspension was added dropwise to a 0° C. solution of aq. NH4OH (19 g/L; 30 mL). The suspension was filtered and the collected solid dried to yield 87 mg (52%) of a crude solid, which was immediately used without purification.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationThe suspension was filtered
  3. customthe collected solid dried

Sources & evidence

ORD record
ord-57c58e29c80c4726aec5cdb55d131f62
Source dataset
uspto-grants-2011_10
Patent number
US08030321B2

Reaction notes

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