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Dimethylformamide → 4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidinylmethyl)carbamoyl]-6-methoxy-2-methylthiopyrimidine

HRID 917649
Notes
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Reaction equation

HRID 917649 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:5][NH:6][C:7]1[C:12]([C:13]([OH:15])=O)=[C:11]([O:16][CH3:17])[N:10]=[C:9]([S:18][CH3:19])[N:8]=1.[NH2:25][CH2:26][C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1.O.ON1C2C=CC=CC=2N=N1.CN(C)C=O>C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:5][NH:6][C:7]1[C:12]([C:13](=[O:15])[NH:25][CH2:26][C:27]2[N:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[C:11]([O:16][CH3:17])[N:10]=[C:9]([S:18][CH3:19])[N:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 27960291-Hydroxybenzotriazole hydrateHCID 46580472-PyrimidinemethanamineHCID 178483244-(3-Chloro-4-methoxybenzylamino)-5-carboxy-6-methoxy-2-methylthiopyrimidine

Product 1

HCID 178483454-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidinylmethyl)carbamoyl]-6-methoxy-2-methylthiopyrimidine

Reagents, catalysts & solvents

1
HCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 4-(3-chloro-4-methoxybenzylamino)-5-carboxy-6-methoxy-2-methylthiopyrimidine (prepared in the above (2)) 183 mg, 2-aminomethylpyrimidine 70 mg, 1-hydroxybenzotriazole hydrate 67 mg and dimethylformamide 4 ml is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimido hydrochloride 114 mg on an ice bath, and the mixture is stirred for 14 hours at room temperature. The reaction mixture is diluted with an aqueous sodium hydrogen carbonate solution 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=20:1→10:1) to give 4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidinylmethyl)carbamoyl]-6-methoxy-2-methylthiopyrimidine as a colorless crystalline powder 208 mg. mp 171-172° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is separated with silica gel chromatography (solvent; chloroform:ethyl acetate=20:1→10:1)

Sources & evidence

ORD record
ord-35a428b6defe481295bbc147e2875751
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07273868B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes