Dimethylformamide dimethyl acetal → HCID 86591394, compound

HRID 897043Notes

Reaction equation

HRID 897043 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[C:12]2[S:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[CH3:18].CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13](=[O:14])[C:12]2[S:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[CH:18]=[CH:21][N:22]([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 901567HCID 901567, compound

Product 1

HCID 86591394HCID 86591394, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-(2-chloro-phenyl)-2-methyl-4-oxo-3,4-dihydro-thieno[3,2-d]pyrimidine (9.4 g, 34.06 mmol) and dimethylformamide dimethyl acetal (9.0, 68.12 mmol) in dimethylformamide (70 mL) was heated to 140° C. for 24 hours. The reaction was cooled to ambient temperature and concentrated at reduced pressure (50° C. bath temperature). The residue was slurried in methanol and concentrated at reduced pressure. This methanol slurry/concentration procedure was repeated twice. The residue was triturated with methanol and the light yellow crystalline solid which formed was collected and dried to give 10.1 g (85%) of 3-(2-chloro-phenyl)-2-(dimethylamino-vinyl)-4-oxo-3,4-dihydro-thieno[3,2-d]pyrimidine which had: 1H NMR δ 7.83 (d, J=12.5 Hz, 1 H), 7.68 (d, J=5 Hz, 1 H), 7.57 (m, 1 H), 7.41 (m, 2 H), 7.31 (m, 1 H), 7.14 (d, J=5 Hz, 1 H), 4.06 (d, J=12.5 Hz, 1 H), 2.77 (br s, 6 H).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated at reduced pressure (50° C. bath temperature)
  3. concentrationconcentrated at reduced pressure
  4. concentrationThis methanol slurry/concentration procedure
  5. customThe residue was triturated with methanol
  6. customthe light yellow crystalline solid which formed
  7. customwas collected
  8. customdried

Sources & evidence

ORD record
ord-fde1f280b73d4e4fbc654ff6735c3c0f
Source dataset
uspto-grants-2005_07
Patent number
US06921764B2

Reaction notes

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