Glycol monoethyl ether → HCID 5328423, compound

HRID 1489602Notes

Reaction equation

HRID 1489602 reaction equation
Cl[C:2]1[C:3]2[S:10][C:9]3[N:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(OCCO)C>>[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH:19][C:2]1[C:3]2[S:10][C:9]3[N:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 8076Glycol monoethyl etherHCID 115623-BromoanilineHCID 27795994-chloropyrido[3',2':4,5]thieno[3,2-d]pyrimidine

Product 1

HCID 5328423HCID 5328423, compoundYield 39.4%

Procedure

A mixture of 4-chloropyrido[3',2'; 4,5]thieno[3,2-d]pyrimidine (72 mg, 0.32 mmol) (see previous experimental), 3-bromoaniline (0.04 mL, 0.37 mmol) and 2-ethoxyethanol (5 mL) is heated under N2 with stirring at 135 C. for 3 h. Upon cooling a solid precipitates. The solid is collected by filtration, washed with acetone and dried in a vacuum oven at ~80 C. to give 4-(3-bromoanilino)pyrido[3',2'; 4,5]thieno[3,2-d]pyrimidine (45 mg, 39.4%). 1H NMR (DMSO) δ9.96 (1H, s), 8.88 (1H, dd, J=4.6, 1.7 Hz), 8.85 (1H, s), 8.72 (1H, dd, J=8.0, 1.7 Hz), 8.20 (1H, t, J=2.0 Hz), 7.84 (1H, ddd, J=8.0, 2.0, 1.3 Hz), 7.69 (1H, dd, J=8.0, 4.7 Hz), 7.39-7.31 (2H, m).

Workup

  1. temperatureis heated under N2
  2. temperatureUpon cooling a solid
  3. customprecipitates
  4. filtrationThe solid is collected by filtration
  5. washwashed with acetone
  6. customdried in a vacuum oven at ~80 C

Sources & evidence

ORD record
ord-93b55f718972436aafd634026ed7e42c
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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