3-Methyluracil → 2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

HRID 1182661

반응식

HRID 1182661 반응식
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][NH:4][C:3]1=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[OH:38][C@@H:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[NH2:44].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[OH:38][C@@H:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[NH:44][C:3]1[N:2]([CH3:1])[C:7](=[O:8])[CH:6]=[CH:5][N:4]=1

참가 물질

6

반응물 4

HCID 790663-MethyluracilHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 12886906(1R,2R)-2-aminocyclopentan-1-ol hydrochloride

생성물 1

HCID 673709162-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one수율 76.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Methyluracil (12.6 mg, 0.1 mmol) was dissolved in 0.5 mL of DMF, and then BOP (71 mg, 0.16 mmol) was added. The mixture was stirred at room temperature for two minutes, then (1R,2R)-(−)-2-hydroxycyclopentylamine hydrochloride salt (22 mg, 0.16 mmol) was added, followed by DBU (51 uL, 3.4 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was purified by a semi-preparative HPLC to give pure product (16 mg, yield 76%). MS (ESI) m/z 210.1 [M+H]+.

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe reaction mixture was purified by a semi-preparative HPLC

출처 및 근거

ORD 기록
ord-b91a2c85966e4a2ba3dd38e25348a084
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664207B2

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