Methanol → 7-(((2RS,3SR)-1,3,4-trihydroxybutan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

HRID 533181노트

반응식

HRID 533181 반응식
C(OC[N:10]1[C:18]2[C:17]([O:19]C(C)(C)C)=[N:16][CH:15]=[N:14][C:13]=2[C:12]([CH2:24][NH:25][CH:26]([CH2:34][O:35]COC)[CH:27]([OH:33])[CH2:28][O:29]COC)=[CH:11]1)C1C=CC=CC=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:35][CH2:34][CH:26]([NH:25][CH2:24][C:12]1[C:13]2[N:14]=[CH:15][NH:16][C:17](=[O:19])[C:18]=2[NH:10][CH:11]=1)[CH:27]([OH:33])[CH2:28][OH:29]

참가 물질

5

반응물 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67024018(6RS,7SR)-7-((5-(benzyloxymethyl)-4-tert-butoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2,4,9,11-tetraoxadodecan-6-ol

생성물 1

HCID 1360362067-(((2RS,3SR)-1,3,4-trihydroxybutan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The product from Example 1.5 (104 mg, 0.195 mmol) was stirred in DCM (10 ml) at −78° C. and boron tribromide (1.0M in DCM, 1.95 ml) added dropwise. The reaction was stirred at −78° C. for 45 minutes before addition of methanol (10 ml). The solvents were evaporated and the residue co-evaporated with methanol (2×). The residue was partitioned between water and DCM and the aqueous layer evaporated. The residue was stirred in methanolic ammonia for 10 minutes and then evaporated on to silica and purified by flash silica chromatography, eluting with 5:4.5:0.5 DCM:methanol:ammonia giving the title compound as a white solid (27 mg, 52%). 1H NMR (300 MHz, CDCl3) 2.76 (1H, q, J 5.2 Hz), 3.48 (1H, dd, J 6.3, 11.9 Hz), 3.60 (2H, m), 3.70 (2H, m), 3.85 (2H, ABq), 7.34 (1H, s), 7.78 (1H, s); 13C NMR (75 MHz, CDCl3) 40.2, 59.8, 59.8, 63.5, 71.2, 113.1, 117.5, 129.2, 142.4, 143.5, 155.4; m/z (ES+) 537 (2MH+, 20%), 269 (MH+, 100%); HRMS (ESI+) C11H16N4O4 requires 269.1241. found 269.1250. The product, compound 1.6, is a 1:1 mixture of the enantiomers of Examples 17 and 18 below.

후처리

  1. customThe solvents were evaporated
  2. customThe residue was partitioned between water and DCM
  3. customthe aqueous layer evaporated
  4. customevaporated on to silica
  5. custompurified by flash silica chromatography
  6. washeluting with 5:4.5:0.5 DCM
  7. additiona 1:1 mixture of the enantiomers of Examples 17 and 18 below

출처 및 근거

ORD 기록
ord-0c2ff33a969f430e83fb8362a68b92eb
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853224B2

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