Dimethylamine → 4-(3-Chloro-anilino)-6-(N,N-dimethyl-carbamoyl)-7H-pyrrolo[2,3-d]-pyrimidin

HRID 369869Notes

Reaction equation

HRID 369869 reaction equation
[C:1]([C:4]1[NH:20][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=3)[C:6]=2[CH:5]=1)([OH:3])=O.[B-](F)(F)(F)F.[CH3:26][N:27](C(ON1C(=O)C=CC=C1)=[N+](C)C)[CH3:28].CNC>CN(C=O)C>[Cl:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[NH:12][C:11]1[C:6]2[CH:5]=[C:4]([C:1](=[O:3])[N:27]([CH3:28])[CH3:26])[NH:20][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate2×HCID 212626746-carboxy-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 232826894-(3-Chloro-anilino)-6-(N,N-dimethyl-carbamoyl)-7H-pyrrolo[2,3-d]-pyrimidin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a N2 atmosphere, 97.6 mg (0.338 mmol) of 6-carboxy-4-(3-chloro-anilino)-7H-pyrrolo[2,3-d]pyrimidine are introduced into 7 ml of DMF, and 119 mg (0.40 mmol) of TPTU and a solution of 164 mg (33% in ethanol; 1.2 mmol) of dimethylamine in 1 ml of DMF are added thereto. After 2 hours, a further 30 mg of TPTU is added to the reaction solution, which is then stirred at RT for 2 days, then poured into 30 ml of ice-water, stirred, filtered and washed with water to yield the title compound; HPLC: tRet (Grad20)=9.5; TLC-Rf =0.38 (CH2Cl2 /methanol [10:1]); FAB-MS: (M+H)+ =316.

Workup

  1. stirringstirred
  2. filtrationfiltered
  3. washwashed with water

Sources & evidence

ORD record
ord-a81a4fed39b14dcf89dcd23eeae12b1a
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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