N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitropyrimidin-4-amine → N4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)pyrimidine-4,5-diamine

HRID 1363246Notes

Reaction equation

HRID 1363246 reaction equation
[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[C@H:22]([NH:30][C:31]2[C:36]([N+:37]([O-])=O)=[CH:35][N:34]=[C:33]([N:40]3[C:44]4[CH:45]=[C:46]([F:49])[CH:47]=[CH:48][C:43]=4[N:42]=[CH:41]3)[N:32]=2)[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.CO>[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[C@H:22]([NH:30][C:31]2[C:36]([NH2:37])=[CH:35][N:34]=[C:33]([N:40]3[C:44]4[CH:45]=[C:46]([F:49])[CH:47]=[CH:48][C:43]=4[N:42]=[CH:41]3)[N:32]=2)[CH2:21][CH2:20]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 59846358N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitropyrimidin-4-amine

Product 1

HCID 59846398N4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)pyrimidine-4,5-diamineYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitropyrimidin-4-amine (633 mg, 0.975 mmol) was dissolved in EtOAc (25 mL) and MeOH (25 mL), and mixed with platium on carbon, sulfided (10%, wet) (127 mg, 20% w/w). The reaction mixture was applied to Parr apparatus under H2 (40 psi) for 5 h. TLC showed the reaction completed. The catalyst was filtered off and washed with MeOH. The filtrate and washings were combined and evaporated to dryness to give a white solid product (498 mg, 82%). MS (ESI): 647.5; 1H NMR (400 MHz, DMSO-d6) δ 8.95 (s, 1H), 8.18 (dd, 1H), 7.63-7.76 (m, 6H), 7.41-7.53 (m, 6H), 7.25-7.30 (m, 1H), 7.02-7.22 (m, 3H), 5.57-5.65 (m, 1H), 4.92 (broad, 2H), 4.87-4.91 (m, 1H), 2.28-2.38 (m, 1H), 1.86-1.98 (m, 2H), 1.72-1.82 (m, 1H), 1.02 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-a4c62677d9524c9faf93f52d302f61aa
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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