Diethanolamine → HCID 54211537, compound

HRID 567753Notes

Reaction equation

HRID 567753 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([CH:15]=O)[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[NH:20]([CH2:24][CH2:25][OH:26])[CH2:21][CH2:22][OH:23]>C(O)C.CN1C(=O)N(C)CCC1.C(O)(=O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]1[C:7]2[CH:14]=[C:13]([CH2:15][N:20]([CH2:24][CH2:25][OH:26])[CH2:21][CH2:22][OH:23])[NH:12][C:8]=2[N:9]=[CH:10][N:11]=1

Participants

7

Reactant 2

HCID 8113DiethanolamineHCID 110976994-(3-chloroanilino)-6-formyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 54211537HCID 54211537, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-CatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

109 mg (0.40 mmol) of 4-(3-chloroanilino)-6-formyl-7H-pyrrolo[2,3-d]pyrimidine (stage 1.6) and 84 mg (0.8 mmol) of diethanolamine in 6 ml of ethanol, 60 drops of DMPU and 50 μl of acetic acid are stirred at RT for a few hours. 30 mg of Raney nickel are then added and the mixture is hydrogenated at 50° C. The catalyst is filtered off and the filtrate is evaporated. Column chromatography (SiO2, CH2Cl2/methanol=10:1) and crystallization from ethyl acetate/diethyl ether yields 4-(3-chloroanilino)-6-[bis(2-hydroxyethyl)aminomethyl]-7H-pyrrolo[2,3-d]pyrimidine; HPLC: tRet(Grad20)=7.0; TLC-Rf=0.1 (CH2Cl2/methanol=10:1); FAB-MS: (M+H)+=362.

Workup

  1. customis hydrogenated at 50° C
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customColumn chromatography (SiO2, CH2Cl2/methanol=10:1) and crystallization from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-5fd63a8504e7441390b1a0fc1fc18a31
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

Loading…