Dimethylformamide → HCID 17848346, compound

HRID 1352788Notes

Reaction equation

HRID 1352788 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:14])=[C:11]([N:26]2[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28][CH2:27]2)[N:10]=[C:9](S(C)=O)[N:8]=1.[NH:41]1[CH2:47][CH2:46][CH2:45][C@H:42]1[CH2:43][OH:44].C(N(CC)CC)C.CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:14])=[C:11]([N:26]2[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28][CH2:27]2)[N:10]=[C:9]([N:41]2[CH2:47][CH2:46][CH2:45][CH:42]2[CH2:43][OH:44])[N:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 640091L-ProlinolHCID 17848288HCID 17848288, compound

Product 1

HCID 17848346HCID 17848346, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of whole amount of 4-(3-chloro-4-methoxybenzylamino)-5-(2-benzyloxyethoxycarbonyl)-6-(4-hydroxypiperidin-1-yl)-2-methylsulfinylpyrimidine (prepared in the above (4)), L-prolinol 53 mg, triethylamine 53 mg and dimethylformamide 4 ml is stirred at room temperature for 1.5 hours and then at 65° C. for 3.5 hours. After cooling the reaction mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate layer is washed, dried and concentrated in vacuo. The residue is separated with silica gel chromatography (solvent; chloroform: ethyl acetate=1:2) to give 4-(3-chloro-4-methoxybenzylamino)-5-(2-benzyloxyethoxycarbonyl)-6-(4-hydroxypiperidin-1-yl)-2-(2-hydroxymethyl-1-pyrrolidinyl)pyrimidine as a colorless caramel 96 mg.

Workup

  1. waitat 65° C. for 3.5 hours
  2. temperatureAfter cooling the reaction mixture
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue is separated with silica gel chromatography (solvent; chloroform: ethyl acetate=1:2)

Sources & evidence

ORD record
ord-5be788c213b14c37a75ade5e8d4fc1c5
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Reaction notes

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