Triethylamine → HCID 21262630, compound

HRID 567766Notes

Reaction equation

HRID 567766 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:24][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=4)[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.CO[CH:27](OC)[N:28]([CH3:30])[CH3:29].C(N(CC)CC)C>C1COCC1>[Cl:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[NH:16][C:15]1[C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:1]=[CH:27][N:28]([CH3:30])[CH3:29])=[CH:3][CH:4]=3)[NH:24][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 21262612HCID 21262612, compound

Product 1

HCID 21262630HCID 21262630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.2 g (0.56 mmol) of 6-(4-aminophenyl)-4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidine (see stage 19.5), 0.097 ml (0.67 mmol) of N,N-dimethylformamide dimethyl acetal and 0.112 ml (0.73 mmol) of triethylamine are stirred at RT for 24 h in 10 ml of THF until all the starting material has disappeared in the TLC. The reaction solution is concentrated to dryness in vacuo and the residue is chromatographed on a silica gel column. Crystallization from THF/hexane or ethyl acetate/hexane gives 4-(3-chloroanilino)-6-(4-[dimethylamino-methylenamino]phenyl)-7H-pyrrolo[2,3-d]pyrimidine; m.p.>300° C.; MS: (M)+=390.

Workup

  1. concentrationThe reaction solution is concentrated to dryness in vacuo
  2. customthe residue is chromatographed on a silica gel column
  3. customCrystallization from THF/hexane or ethyl acetate/hexane

Sources & evidence

ORD record
ord-a09fc1472faf4f58bcf765f4eb0dc1ae
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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