Ammonia → HCID 86715518, compound

HRID 2284604Notes

Reaction equation

HRID 2284604 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]=[CH:20][NH:21][C:22](=O)[C:23]=4[N:24]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[N:26]1P(Cl)(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=NP=1(Cl)Cl.CCN(C(C)C)C(C)C.N>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([C:15]3[CH:16]=[CH:17][C:18]4[N:19]=[CH:20][N:21]=[C:22]([NH2:26])[C:23]=4[N:24]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 762851,3,5,7,2,4,6,8-Tetrazatetraphosphocine, 2,2,4,4,6,6,8,8-octachloro-2,2,4,4,6,6,8,8-octahydro-HCID 81531DiisopropylethylamineHCID 136408031HCID 136408031, compound

Product 1

HCID 86715518HCID 86715518, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-(2-(3-Chloro-4-fluorophenyl)pyridin-3-yl)pyrido[3,2-d]pyrimidin-4 (3H)-one (100 mg, 0.28 mmol), phosphonitrilic chloride (100 mg, 0.28 mmol) and as stir bar were transferred to a vial, capped and placed under nitrogen atmosphere. Dry acetonitrile (3 mL) was transferred and allowed the contents to stir at room temperature. i-Pr2NEt was added for 2 min to the heterogeneous slurry. Upon stirring the red homogeneous slurry for 2 h, nitrogen balloon was replaced with NH3 balloon and stirred. After stirring the contents for 6 h, the reaction mixture was concentrated and the crude residue was partitioned between chloroform/water. Organic layer was removed and re-extracted the aqueous layer with chloroform. Usual workup and purification by preparative HPLC provided 6-(2-(3-Chloro-4-fluorophenyl)pyridin-3-yl)pyrido[3,2-d]pyrimidin-4-amine (16 mg) as a white solid.

Workup

  1. customcapped
  2. stirringUpon stirring the red homogeneous slurry for 2 h
  3. stirringstirred
  4. stirringAfter stirring the contents for 6 h
  5. concentrationthe reaction mixture was concentrated
  6. customthe crude residue was partitioned between chloroform/water
  7. customOrganic layer was removed
  8. extractionre-extracted the aqueous layer with chloroform
  9. customUsual workup and purification by preparative HPLC

Sources & evidence

ORD record
ord-ce1dde7a64314c59919b6e9665bbdbb3
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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