(1-Aminocyclopropyl)methanol → [1-(2-chloro-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-1-ylamino)-cyclopropyl]-methanol

HRID 70093Notes

Reaction equation

HRID 70093 reaction equation
ClC1N=C(Cl)C2SCCC=2N=1.[NH2:12][C:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1.[Cl:18][C:19]1[N:20]=[C:21](NC2(CO)CC2)[C:22]2[S:27](=[O:28])[CH2:26][CH2:25][C:23]=2[N:24]=1>>[Cl:18][CH:19]1[N:24]([NH:12][C:13]2([CH2:16][OH:17])[CH2:15][CH2:14]2)[C:23]2[CH2:25][CH2:26][S:27](=[O:28])[C:22]=2[CH:21]=[N:20]1

Participants

4

Reactant 3

HCID 14146220(1-Aminocyclopropyl)methanolHCID 457899672,4-Dichloro-6,7-dihydrothieno[3,2-d]pyrimidineHCID 59708399[1-(2-chloro-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-methanol

Product 1

HCID 86706876[1-(2-chloro-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-1-ylamino)-cyclopropyl]-methanol

Procedure

Starting from 2,4-dichloro-6,7-dihydro-thieno[3,2-d]pyrimidine and 1-amino-cyclopropanmethanol the two enantiomers of [1-(2-chloro-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-methanol may be prepared as described in Example 28 (cf 2.1.2). The enantiomers may be separated by chiral HPLC (column Diacel IA, 250×4.6 mm, 5 m, eluant: (hexane+cyclohexylamine (0.2%))/ethanol (80/20), flow rate: 1 ml/min): enantiomer 1: RT=11.1 min; enantiomer 2: RT=16.5 min.

Workup

  1. custommay be prepared
  2. customThe enantiomers may be separated by chiral HPLC (column Diacel IA, 250×4.6 mm, 5 m, eluant: (hexane+cyclohexylamine (0.2%))/ethanol (80/20), flow rate: 1 ml/min)

Sources & evidence

ORD record
ord-a4ef11e545474a9b8b34c1287a4952dc
Source dataset
uspto-grants-2014_09
Patent number
US08822474B2

Reaction notes

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