Diisopropylethylamine → (2-Chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-yl)-(3-morpholin-4-ylmethyl-phenyl)-amine

HRID 70083Notes

Reaction equation

HRID 70083 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[N:21]1([CH2:27][C:28]2[CH:29]=[C:30]([NH2:34])[CH:31]=[CH:32][CH:33]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>CN(C)C=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:34][C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([CH2:27][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[CH:29]=2)[C:5]2[S:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10964063-(Morpholin-4-ylmethyl)anilineHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidine

Product 1

HCID 59708440(2-Chloro-6,7-dihydro-thieno[3,2-d]pyrimidin-4-yl)-(3-morpholin-4-ylmethyl-phenyl)-amineYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.25 g 2,4-dichloro-6,7-dihydro-thieno[3,2-d]pyrimidine are placed in 5 ml dimethylformamide, first 1.05 ml diisopropylethylamine, then 0.960 g 3-morpholin-4-ylmethyl-phenylamine (J. Med. Chem. 1990, 33, 327) are added. The reaction mixture is sf 20 hours at 60° C., then after cooling evaporated down. The residue is extracted with dichloromethane and water, the organic phase is dried and evaporated to dryness. The residue is crystallised with petroleum ether/ethyl acetate. 1.28 g of the product are obtained as a powder.

Workup

  1. temperatureafter cooling
  2. customevaporated down
  3. extractionThe residue is extracted with dichloromethane and water
  4. customthe organic phase is dried
  5. customevaporated to dryness
  6. customThe residue is crystallised with petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-13aa5ad1abcf4b738ee9dfdee5adc231
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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