1,8-Diazabicyclo(5.4.0)undec-7-ene → Ethyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide

HRID 1181237Notes

Reaction equation

HRID 1181237 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:3]=1.C1CCN2C(=NCCC2)CC1.[CH2:35]([NH:37][S:38](Cl)(=[O:40])=[O:39])[CH3:36]>C1COCC1.C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:17][C:6]1[N:5]=[C:4]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[N:3]=[C:2]([NH:1][S:38](=[O:40])(=[O:39])[NH:37][CH2:35][CH3:36])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11040810Ethylsulfamoyl chlorideHCID 219795734-Amino-6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)pyrimidine

Product 1

HCID 21979572Ethyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (100 mg) was dissolved in THF (5 ml) and DCM (5 ml). DBU (46 mg) and DMAP (37 mg) were added followed by the addition of ethyl-sulfamoylchloride (prepared from ethylamine hydrochloride and sulfuryl chloride). The mixture was stirred for 12 h at r.t. The solvent was evaporated. Water and a 10% solution of citric acid were added followed by extraction with EtOAc and DCM. The combined organic layers were dried over sodium sulfate and the solvent was evaporated under reduced pressure. After purification of the residue by chromatography over silicagel with EtOAc/methanol/ammonia=4:1:0.5, ethyl sulfamic acid-[6-chloro-5-(o-methoxy-phenoxy)-2-(4-pyridyl)pyrimidin-4-yl]-amide (10 mg) was obtained. tR=4.31 min, (LC); [M+H]+=436.14 (ES+).

Workup

  1. customThe solvent was evaporated
  2. additionWater and a 10% solution of citric acid were added
  3. extractionfollowed by extraction with EtOAc and DCM
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customAfter purification of the residue by chromatography over silicagel with EtOAc/methanol/ammonia=4:1:0.5

Sources & evidence

ORD record
ord-958a5e9933ee42ccbe18d6841927cc82
Source dataset
uspto-grants-2007_10
Patent number
US07285549B2

Reaction notes

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