Bromomethyl 4-methoxyphenyl ketone → 4-(3-chloroanilino)-6-[4-(4-methoxyphenyl)thiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 567760Notes

Reaction equation

HRID 567760 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15](=[S:17])[NH2:16])[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[CH3:21][O:22][C:23]1[CH:32]=[CH:31][C:26]([C:27](=O)[CH2:28]Br)=[CH:25][CH:24]=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([C:15]3[S:17][CH:28]=[C:27]([C:26]4[CH:31]=[CH:32][C:23]([O:22][CH3:21])=[CH:24][CH:25]=4)[N:16]=3)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 212626564-(3-chloroanilino)-6-(thiocarbamoyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 1357028394-(3-chloroanilino)-6-[4-(4-methoxyphenyl)thiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

57.5 mg (0.19 mmol) of 4-(3-chloroanilino)-6-(thiocarbamoyl)-7H-pyrrolo[2,3-d]pyrimidine (see Example 10) in 3 ml of methanol and 57.3 mg (0.25 mmol) of 4-methoxyphenacyl bromide are heated to boiling for 17 h. Cooling of the pale yellow suspension, filtering and washing with isopropanol/diethyl ether yields 4-(3-chloroanilino)-6-[4-(4-methoxyphenyl)thiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=15.4; TLC-Rf=0.33 (CH2Cl2/methanol=10:1); FAB-MS: (M+H)+=434.

Workup

  1. temperatureCooling of the pale yellow suspension
  2. filtrationfiltering
  3. washwashing with isopropanol/diethyl ether

Sources & evidence

ORD record
ord-ec5d86f74a704fa2940eb2b8d8caf062
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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