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Isobutyraldehyde → tert-butyl N-[4-[[[(6S)-3-[bis(2-methylpropyl)amino]-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

HRID 10964
Notes
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Reaction equation

HRID 10964 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([C@H:20]2[N:24]3[C:25](=[O:37])[C:26]([NH:29][CH2:30][C:31]4[CH:36]=CC=C[CH:32]=4)=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[C:39](OC(=O)NC(C1C=CC(CNC([C@H]2N3C(=O)C(N)=CN=C3CC2)=O)=CC=1)=N)([CH3:42])([CH3:41])[CH3:40].C(=O)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([C@H:20]2[N:24]3[C:25](=[O:37])[C:26]([N:29]([CH2:40][CH:39]([CH3:42])[CH3:41])[CH2:30][CH:31]([CH3:36])[CH3:32])=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=[NH:9])([CH3:2])([CH3:4])[CH3:3]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 145857226tert-butyl N-[4-[[[(6S)-3-amino-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamateHCID 145857234tert-butyl N-[4-[[[(6S)-3-(benzylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 145857206
tert-butyl N-[4-[[[(6S)-3-[bis(2-methylpropyl)amino]-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate
Yield 79.5%

Procedure

Following a procedure similar to that for the preparation of intermediate 1k, intermediate 1j (97.1 mg, 0.228 mmol), isobutyraldehyde (32.8 mg, 0.455 mmol) and NaBH(OAc)3 (135.1 mg, 0.638 mmol) yielded 87.4 mg (79.5%) of intermediate 9a. MS (ESI) 539.2 (M+H+).

Sources & evidence

ORD record
ord-8ae7b2d9548841909fb347af3a2a420c
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094783B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes